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BORRELIDIN

  • Product Name BORRELIDIN
  • cas 7184-60-3
  • purity 99%
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Manufacturer Supply Best Quality BORRELIDIN 7184-60-3 with Efficient Transportation

  • Molecular Formula: C28H43NO6
  • Molecular Weight: 489.653
  • Appearance/Colour: White to off-white powder 
  • Vapor Pressure: 2.6E-23mmHg at 25°C 
  • Melting Point: 143-145℃ 
  • Refractive Index: 1.538 
  • Boiling Point: 710.3 °C at 760 mmHg 
  • PKA: 4.56±0.40(Predicted) 
  • Flash Point: 383.4 °C 
  • PSA： 127.85000 
  • Density: 1.14 g/cm3 
  • LogP: 4.63558 

BORRELIDIN(Cas 7184-60-3) Usage

Biochem/physiol Actions

Borrelidin is a potent angiogenesis inhibitor that induces apoptosis in capillary tube-forming cells. Also displays antimalarial activity against drug-resistant Plasmodia. Antimicrobial and selective threonyl t-RNA synthetase inhibitor.

Definition

ChEBI: A macrolide that is isolated from several Streptomyces species and displays antibiotic, antineoplastic and antimalarial properties.

General Description

Chemical structure: macrolide

InChI:InChI=1/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1

7184-60-3 Relevant articles

Total synthesis of borrelidin

Nagamitsu, Tohru,Takano, Daisuke,Marumoto, Kaori,Fukuda, Takeo,Furuya, Kentaro,Otoguro, Kazuhiko,Takeda, Kazuyoshi,Kuwajima, Isao,Harigaya, Yoshihiro,Omura, Satoshi

, p. 2744 - 2756 (2008/02/05)

(Chemical Equation Presented) The total ...

Total synthesis of (-)-borrelidin

Nagamitsu, Tohru,Takano, Daisuke,Fukuda, Takeo,Otoguro, Kazuhiko,Kuwajima, Isao,Harigaya, Yoshihiro,Omura, Satoshi

, p. 1865 - 1867 (2007/10/03)

Matrix presented. The total synthesis of...

Stereoselective total synthesis of (-)-borrelidin

Vong, Binh G.,Kim, Sun Hee,Abraham, Sunny,Theodorakis, Emmanuel A.

, p. 3947 - 3951 (2007/10/03)

A convergent synthesis of (-)-borrelidin...

Application of Conformation Design in Acyclic Stereoselection: Total Synthesis of Borrelidin as the Crystalline Benzene Solvate

Hanessian, Stephen,Yang, Yang,Giroux, Simon,Mascitti, Vincent,Ma, Jianguo,Raeppel, Franck

, p. 13784 - 13792 (2007/10/03)

The total synthesis of (-)-borrelidin (t...

7184-60-3 Process route

(1'R,1S,2S,2'R,8R,9S,11R,13S,15S,16S)-2-(7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentane-1'-carboxylic acid 2-trimethylsilanyl-ethyl ester
631919-63-6

(1'R,1S,2S,2'R,8R,9S,11R,13S,15S,16S)-2-(7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentane-1'-carboxylic acid 2-trimethylsilanyl-ethyl ester

borrelidin
7184-60-3,97328-74-0

borrelidin

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h;
94%
(1R,2R)-1,2-(dihydroxymethyl)cyclopentane
57287-24-8

(1R,2R)-1,2-(dihydroxymethyl)cyclopentane

borrelidin
7184-60-3,97328-74-0

borrelidin

Conditions
Conditions Yield
Multi-step reaction with 26 steps
1.1: NaH / dimethylformamide / -20 - 20 °C
2.1: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C
4.1: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5.1: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6.1: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7.1: 73 percent / benzene / 48 h / 80 °C
8.1: 84 percent / benzene / 39 h / 70 °C
9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C
10.1: 452 mg / Et3 N; DMAP / benzene / 2 h / 20 °C
11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2 Cl2 / 1.5 h / 20 °C
13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
13.2: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
14.1: DMAP / pentane / 168 h / 20 °C
14.2: 31.2 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.5 h / 0 °C
15.1: 85 percent / 2,6-lutidine / CH2 Cl2 / 0.5 h / 0 °C
16.1: 85 percent / NaBH4 / Pd(PPh3 )4 / methanol / 0.5 h / 0 °C
17.1: 69 percent / NH3 ; Et3 N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2 Cl2 / 1.5 h / 20 °C
19.1: 73 percent / K2 CO3 ; MeOH / 1.5 h / 20 °C
20.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
21.1: 8.50 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.08 h / 0 °C
22.1: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
23.1: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
24.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
25.1: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; methanol; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; ammonia; water; pyridinium p-toluenesulfonate; 2-chloro-1,3-dimethylimidazolinium chloride; sodium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; pentane; benzene; 2.1: Dess-Martin oxidation / 7.1: Wittig reaction / 8.1: Wittig reaction / 13.2: Dess-Martin oxidation / 20.1: Dess-Martin oxidation / 24.1: Dess-Martin oxidation;
Multi-step reaction with 25 steps
1.1: NaH / dimethylformamide / -20 - 20 °C
2.1: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C
4.1: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5.1: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6.1: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7.1: 73 percent / benzene / 48 h / 80 °C
8.1: 84 percent / benzene / 39 h / 70 °C
9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C
10.1: 452 mg / Et3 N; DMAP / benzene / 2 h / 20 °C
11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2 Cl2 / 1.5 h / 20 °C
13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
13.2: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
14.1: DMAP / pentane / 168 h / 20 °C
14.2: 31.2 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.5 h / 0 °C
15.1: 85 percent / 2,6-lutidine / CH2 Cl2 / 0.5 h / 0 °C
16.1: 85 percent / NaBH4 / Pd(PPh3 )4 / methanol / 0.5 h / 0 °C
17.1: 69 percent / NH3 ; Et3 N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
18.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2 Cl2 / 1.5 h / 20 °C
19.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
20.1: 8.50 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.08 h / 0 °C
21.1: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
22.1: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
23.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
24.1: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; ammonia; water; pyridinium p-toluenesulfonate; 2-chloro-1,3-dimethylimidazolinium chloride; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; pentane; benzene; 2.1: Dess-Martin oxidation / 7.1: Wittig reaction / 8.1: Wittig reaction / 13.2: Dess-Martin oxidation / 19.1: Dess-Martin oxidation / 23.1: Dess-Martin oxidation;
Multi-step reaction with 18 steps
1: NaH / dimethylformamide / -20 - 20 °C
2: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3: 54 percent / tetrahydrofuran / 0.5 h / -78 °C
4: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7: 73 percent / benzene / 48 h / 80 °C
8: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C
9: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
10: 204 mg / Et3 N; DMAP / benzene / 0.5 h / 20 °C
11: 93 percent / PPTS / ethanol / 10 h / 50 °C
12: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2 Cl2 / 0.5 h / 20 °C
13: 21 percent / SmI2 ; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C
14: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
15: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
16: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
17: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
18: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; water; oxygen; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 2: Dess-Martin oxidation / 7: Wittig reaction / 16: Dess-Martin oxidation;
Multi-step reaction with 20 steps
1: NaH / dimethylformamide / -20 - 20 °C
2: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3: 54 percent / tetrahydrofuran / 0.5 h / -78 °C
4: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7: 73 percent / benzene / 48 h / 80 °C
8: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C
9: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
10: 204 mg / Et3 N; DMAP / benzene / 0.5 h / 20 °C
11: 93 percent / PPTS / ethanol / 10 h / 50 °C
12: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2 Cl2 / 0.5 h / 20 °C
13: 19 percent / SmI2 ; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C
14: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
15: 8.50 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.08 h / 0 °C
16: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
17: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
18: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
19: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
20: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; water; oxygen; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 2: Dess-Martin oxidation / 7: Wittig reaction / 14: Dess-Martin oxidation / 18: Dess-Martin oxidation;
Multi-step reaction with 26 steps
1.1: NaH / dimethylformamide / -20 - 20 °C
2.1: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3.1: 33 percent / toluene / 1 h / -78 - 0 °C
4.1: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5.1: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6.1: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7.1: 73 percent / benzene / 48 h / 80 °C
8.1: 84 percent / benzene / 39 h / 70 °C
9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C
10.1: 452 mg / Et3 N; DMAP / benzene / 2 h / 20 °C
11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2 Cl2 / 1.5 h / 20 °C
13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
13.2: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
14.1: DMAP / pentane / 168 h / 20 °C
14.2: 31.2 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.5 h / 0 °C
15.1: 85 percent / 2,6-lutidine / CH2 Cl2 / 0.5 h / 0 °C
16.1: 85 percent / NaBH4 / Pd(PPh3 )4 / methanol / 0.5 h / 0 °C
17.1: 69 percent / NH3 ; Et3 N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2 Cl2 / 1.5 h / 20 °C
19.1: 73 percent / K2 CO3 ; MeOH / 1.5 h / 20 °C
20.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
21.1: 8.50 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.08 h / 0 °C
22.1: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
23.1: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
24.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
25.1: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; methanol; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; ammonia; water; pyridinium p-toluenesulfonate; 2-chloro-1,3-dimethylimidazolinium chloride; sodium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; pentane; benzene; 2.1: Dess-Martin oxidation / 7.1: Wittig reaction / 8.1: Wittig reaction / 13.2: Dess-Martin oxidation / 20.1: Dess-Martin oxidation / 24.1: Dess-Martin oxidation;
Multi-step reaction with 25 steps
1.1: NaH / dimethylformamide / -20 - 20 °C
2.1: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3.1: 33 percent / toluene / 1 h / -78 - 0 °C
4.1: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5.1: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6.1: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7.1: 73 percent / benzene / 48 h / 80 °C
8.1: 84 percent / benzene / 39 h / 70 °C
9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C
10.1: 452 mg / Et3 N; DMAP / benzene / 2 h / 20 °C
11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2 Cl2 / 1.5 h / 20 °C
13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
13.2: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
14.1: DMAP / pentane / 168 h / 20 °C
14.2: 31.2 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.5 h / 0 °C
15.1: 85 percent / 2,6-lutidine / CH2 Cl2 / 0.5 h / 0 °C
16.1: 85 percent / NaBH4 / Pd(PPh3 )4 / methanol / 0.5 h / 0 °C
17.1: 69 percent / NH3 ; Et3 N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
18.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2 Cl2 / 1.5 h / 20 °C
19.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
20.1: 8.50 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.08 h / 0 °C
21.1: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
22.1: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
23.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
24.1: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; ammonia; water; pyridinium p-toluenesulfonate; 2-chloro-1,3-dimethylimidazolinium chloride; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; pentane; benzene; 2.1: Dess-Martin oxidation / 7.1: Wittig reaction / 8.1: Wittig reaction / 13.2: Dess-Martin oxidation / 19.1: Dess-Martin oxidation / 23.1: Dess-Martin oxidation;
Multi-step reaction with 18 steps
1: NaH / dimethylformamide / -20 - 20 °C
2: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3: 33 percent / toluene / 1 h / -78 - 0 °C
4: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7: 73 percent / benzene / 48 h / 80 °C
8: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C
9: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
10: 204 mg / Et3 N; DMAP / benzene / 0.5 h / 20 °C
11: 93 percent / PPTS / ethanol / 10 h / 50 °C
12: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2 Cl2 / 0.5 h / 20 °C
13: 21 percent / SmI2 ; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C
14: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
15: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
16: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
17: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
18: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; water; oxygen; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene; 2: Dess-Martin oxidation / 7: Wittig reaction / 16: Dess-Martin oxidation;
Multi-step reaction with 20 steps
1: NaH / dimethylformamide / -20 - 20 °C
2: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3: 33 percent / toluene / 1 h / -78 - 0 °C
4: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7: 73 percent / benzene / 48 h / 80 °C
8: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C
9: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
10: 204 mg / Et3 N; DMAP / benzene / 0.5 h / 20 °C
11: 93 percent / PPTS / ethanol / 10 h / 50 °C
12: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2 Cl2 / 0.5 h / 20 °C
13: 19 percent / SmI2 ; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C
14: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
15: 8.50 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.08 h / 0 °C
16: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
17: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
18: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
19: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
20: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; water; oxygen; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene; 2: Dess-Martin oxidation / 7: Wittig reaction / 14: Dess-Martin oxidation / 18: Dess-Martin oxidation;
Multi-step reaction with 26 steps
1.1: NaH / dimethylformamide / -20 - 20 °C
2.1: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3.1: 90 percent / MgBr2 *Et2 O / CH2 Cl2 / 7 h / 0 °C
4.1: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5.1: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6.1: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7.1: 73 percent / benzene / 48 h / 80 °C
8.1: 84 percent / benzene / 39 h / 70 °C
9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C
10.1: 452 mg / Et3 N; DMAP / benzene / 2 h / 20 °C
11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2 Cl2 / 1.5 h / 20 °C
13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
13.2: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
14.1: DMAP / pentane / 168 h / 20 °C
14.2: 31.2 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.5 h / 0 °C
15.1: 85 percent / 2,6-lutidine / CH2 Cl2 / 0.5 h / 0 °C
16.1: 85 percent / NaBH4 / Pd(PPh3 )4 / methanol / 0.5 h / 0 °C
17.1: 69 percent / NH3 ; Et3 N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2 Cl2 / 1.5 h / 20 °C
19.1: 73 percent / K2 CO3 ; MeOH / 1.5 h / 20 °C
20.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
21.1: 8.50 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.08 h / 0 °C
22.1: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
23.1: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
24.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
25.1: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; methanol; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; ammonia; water; pyridinium p-toluenesulfonate; 2-chloro-1,3-dimethylimidazolinium chloride; sodium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; pentane; benzene; 2.1: Dess-Martin oxidation / 7.1: Wittig reaction / 8.1: Wittig reaction / 13.2: Dess-Martin oxidation / 20.1: Dess-Martin oxidation / 24.1: Dess-Martin oxidation;
Multi-step reaction with 25 steps
1.1: NaH / dimethylformamide / -20 - 20 °C
2.1: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3.1: 90 percent / MgBr2 *Et2 O / CH2 Cl2 / 7 h / 0 °C
4.1: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5.1: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6.1: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7.1: 73 percent / benzene / 48 h / 80 °C
8.1: 84 percent / benzene / 39 h / 70 °C
9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C
10.1: 452 mg / Et3 N; DMAP / benzene / 2 h / 20 °C
11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2 Cl2 / 1.5 h / 20 °C
13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
13.2: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
14.1: DMAP / pentane / 168 h / 20 °C
14.2: 31.2 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.5 h / 0 °C
15.1: 85 percent / 2,6-lutidine / CH2 Cl2 / 0.5 h / 0 °C
16.1: 85 percent / NaBH4 / Pd(PPh3 )4 / methanol / 0.5 h / 0 °C
17.1: 69 percent / NH3 ; Et3 N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
18.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2 Cl2 / 1.5 h / 20 °C
19.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
20.1: 8.50 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.08 h / 0 °C
21.1: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
22.1: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
23.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
24.1: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; ammonia; water; pyridinium p-toluenesulfonate; 2-chloro-1,3-dimethylimidazolinium chloride; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; pentane; benzene; 2.1: Dess-Martin oxidation / 7.1: Wittig reaction / 8.1: Wittig reaction / 13.2: Dess-Martin oxidation / 19.1: Dess-Martin oxidation / 23.1: Dess-Martin oxidation;
Multi-step reaction with 18 steps
1: NaH / dimethylformamide / -20 - 20 °C
2: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3: 90 percent / MgBr2 *Et2 O / CH2 Cl2 / 7 h / 0 °C
4: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7: 73 percent / benzene / 48 h / 80 °C
8: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C
9: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
10: 204 mg / Et3 N; DMAP / benzene / 0.5 h / 20 °C
11: 93 percent / PPTS / ethanol / 10 h / 50 °C
12: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2 Cl2 / 0.5 h / 20 °C
13: 21 percent / SmI2 ; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C
14: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
15: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
16: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
17: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
18: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; water; oxygen; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; magnesium bromide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 2: Dess-Martin oxidation / 7: Wittig reaction / 16: Dess-Martin oxidation;
Multi-step reaction with 20 steps
1: NaH / dimethylformamide / -20 - 20 °C
2: 6.24 g / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
3: 90 percent / MgBr2 *Et2 O / CH2 Cl2 / 7 h / 0 °C
4: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
5: H2 O; NMO; OsO4 / acetone / 4 h / 20 °C
6: 533 mg / NaIO4 ; H2 O / methanol / 2 h / 0 °C
7: 73 percent / benzene / 48 h / 80 °C
8: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C
9: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
10: 204 mg / Et3 N; DMAP / benzene / 0.5 h / 20 °C
11: 93 percent / PPTS / ethanol / 10 h / 50 °C
12: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2 Cl2 / 0.5 h / 20 °C
13: 19 percent / SmI2 ; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C
14: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
15: 8.50 mg / NaBH4 ; CeCl3 *7H2 O / methanol / 0.08 h / 0 °C
16: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
17: 90 percent / DDQ; H2 O / CH2 Cl2 / 0.25 h / 0 °C
18: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
19: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O / 0.5 h / 20 °C
20: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; water; oxygen; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; magnesium bromide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 2: Dess-Martin oxidation / 7: Wittig reaction / 14: Dess-Martin oxidation / 18: Dess-Martin oxidation;
Multi-step reaction with 19 steps
1.1: sodium hydride / dimethylformamide / -20 - 20 °C
1.2: 89 percent / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
2.1: 90 percent / MgBr2 *Et2 O / CH2 Cl2 / 7 h / 0 °C
3.1: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
4.1: OsO4 ; N-methylmorpholine N-oxide / acetone; H2 O / 4 h / 20 °C
5.1: 532.7 mg / sodium metaperiodate / methanol; H2 O / 2 h / 0 °C
6.1: 73 percent / benzene / 48 h / 80 °C
7.1: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C
8.1: 94 percent / HF*pyridine / tetrahydrofuran / 48 h / 20 °C
9.1: 97 percent / 4-(dimethylamino)pyridine / benzene / 0.5 h / 20 °C
10.1: 93 percent / PPTS / ethanol / 10 h / 50 °C
11.1: 79 percent / N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / CH2 Cl2 / 0.5 h / 20 °C
12.1: 19 percent / SmI2 ; HMPA / tetrahydrofuran / 0.5 h / -78 °C
13.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
14.1: 8.5 mg / CeCl3 *7H2 O; NaBH4 / methanol / 0.17 h / 0 °C
15.1: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
16.1: 90 percent / DDQ / CH2 Cl2 ; H2 O / 0.25 h / 0 °C
17.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
18.1: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / H2 O; 2-methyl-propan-2-ol / 0.5 h / 20 °C
19.1: 5.2 mg / HF*pyridine / tetrahydrofuran / 48 h / 20 °C
With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; magnesium bromide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 6.1: Wittig reaction / 7.1: Horner-Emmons olefination / 12.1: Reformatsky reaction;
Multi-step reaction with 17 steps
1.1: sodium hydride / dimethylformamide / -20 - 20 °C
1.2: 89 percent / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
2.1: 90 percent / MgBr2 *Et2 O / CH2 Cl2 / 7 h / 0 °C
3.1: 99 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
4.1: OsO4 ; N-methylmorpholine N-oxide / acetone; H2 O / 4 h / 20 °C
5.1: 532.7 mg / sodium metaperiodate / methanol; H2 O / 2 h / 0 °C
6.1: 73 percent / benzene / 48 h / 80 °C
7.1: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C
8.1: 94 percent / HF*pyridine / tetrahydrofuran / 48 h / 20 °C
9.1: 97 percent / 4-(dimethylamino)pyridine / benzene / 0.5 h / 20 °C
10.1: 93 percent / PPTS / ethanol / 10 h / 50 °C
11.1: 79 percent / N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / CH2 Cl2 / 0.5 h / 20 °C
12.1: 21 percent / SmI2 ; HMPA / tetrahydrofuran / 0.5 h / -78 °C
13.1: 75 percent / 2,6-lutidine / CH2 Cl2 / 1 h / 0 °C
14.1: 90 percent / DDQ / CH2 Cl2 ; H2 O / 0.25 h / 0 °C
15.1: Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 20 °C
16.1: NaClO2 ; NaH2 PO4 *2H2 O; 2-methyl-2-butene / H2 O; 2-methyl-propan-2-ol / 0.5 h / 20 °C
17.1: 5.2 mg / HF*pyridine / tetrahydrofuran / 48 h / 20 °C
With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; magnesium bromide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 6.1: Wittig reaction / 7.1: Horner-Emmons olefination / 12.1: Reformatsky reaction;
Multi-step reaction with 26 steps
1.1: 84 percent / imidazole; DMAP / CH2 Cl2 / 8 h / 25 °C
2.1: 89 percent / Dess-Martin periodinane / CH2 Cl2 / 1 h / 25 °C
3.1: toluene / 1 h / -78 °C
3.2: NaH / tetrahydrofuran / 1 h / 0 °C
3.3: TBAI / tetrahydrofuran / 12 h / 25 °C
4.1: 93 percent / TBAF / tetrahydrofuran / 12 h / 25 °C
5.1: 93 percent / iPr2 NEt / CH2 Cl2 / 8 h / 0 - 25 °C
6.1: OsO4 ; NMO; pyridine / acetone; H2 O / 12 h / 25 °C
6.2: 91 percent / NaIO4 / tetrahydrofuran; H2 O / 2 h / 25 °C
7.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C
7.2: 77 percent / tetrahydrofuran / 2 h / -78 °C
8.1: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C
9.1: 91 percent / DDQ / CH2 Cl2 / 1 h / 25 °C / pH 7.0
10.1: 93 percent / imidazole; DMAP / CH2 Cl2 / 8 h / 40 °C
11.1: n-BuLi / hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 0.5 h / -78 °C
11.2: hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / -78 °C
12.1: Ph2 S / sunlight
13.1: 98 percent / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 25 °C
14.1: 89 percent / DDQ / H2 O; CH2 Cl2 / 0.5 h / 25 °C / pH 7.0
15.1: 94 percent / TEMPO; bis(acetoxy)iodobenzene / CH2 Cl2 / 2 h / 25 °C
16.1: BF3 *OEt2 / tetrahydrofuran / 1 h / -78 °C
17.1: 86 percent / iPr2 NEt / CH2 Cl2 / 12 h / 25 °C
18.1: 88 percent / HF*pyridine / tetrahydrofuran / 12 h / 25 °C
19.1: 83 percent / CF3 COOH / CH2 Cl2 / 3 h / 0 °C
20.1: Et3 N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 25 °C
20.2: 59 percent / DMAP / tetrahydrofuran; toluene / 12 h / 25 °C
21.1: hydroquinone; nBu3 SnH / Mo(CO)3(tBuNC)3 / tetrahydrofuran / 12 h / 55 °C
21.2: 54 percent / I2 / CH2 Cl2 / 25 °C
22.1: 90 percent / CuI / Pd(PPh3 )4 / toluene / 8 h / 80 °C
23.1: 69 percent / Me2 BBr / CH2 Cl2 / 2 h / -78 °C
24.1: 85 percent / TEMPO; TCCA / CH2 Cl2 / 1 h / 25 °C
25.1: NaClO2 ; NaH2 PO4 ; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O; tetrahydrofuran / 0.5 h / 25 °C
26.1: NaBH4 ; CeCl3 *7H2 O / methanol / 1 h / 0 °C
With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; cerium(III) chloride; 2-methyl-but-2-ene; dimethylboron bromide; [bis(acetoxy)iodo]benzene; diphenyl sulfide; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; hydroquinone; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium(0); Mo(CO)3(CN-t-Bu)3; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 2.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation / 16.1: Mukaiyama reaction / 20.1: Yamaguchi reaction / 26.1: Luche reaction;
Multi-step reaction with 25 steps
1.1: 84 percent / imidazole; DMAP / CH2 Cl2 / 8 h / 25 °C
2.1: 89 percent / Dess-Martin periodinane / CH2 Cl2 / 1 h / 25 °C
3.1: toluene / 1 h / -78 °C
3.2: NaH / tetrahydrofuran / 1 h / 0 °C
3.3: TBAI / tetrahydrofuran / 12 h / 25 °C
4.1: 93 percent / TBAF / tetrahydrofuran / 12 h / 25 °C
5.1: 93 percent / iPr2 NEt / CH2 Cl2 / 8 h / 0 - 25 °C
6.1: OsO4 ; NMO; pyridine / acetone; H2 O / 12 h / 25 °C
6.2: 91 percent / NaIO4 / tetrahydrofuran; H2 O / 2 h / 25 °C
7.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C
7.2: 77 percent / tetrahydrofuran / 2 h / -78 °C
8.1: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C
9.1: 91 percent / DDQ / CH2 Cl2 / 1 h / 25 °C / pH 7.0
10.1: 93 percent / imidazole; DMAP / CH2 Cl2 / 8 h / 40 °C
11.1: n-BuLi / hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 0.5 h / -78 °C
11.2: hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / -78 °C
12.1: 98 percent / Dess-Martin periodinane / CH2 Cl2 / 0.5 h / 25 °C
13.1: 89 percent / DDQ / H2 O; CH2 Cl2 / 0.5 h / 25 °C / pH 7.0
14.1: 94 percent / TEMPO; bis(acetoxy)iodobenzene / CH2 Cl2 / 2 h / 25 °C
15.1: BF3 *OEt2 / tetrahydrofuran / 1 h / -78 °C
16.1: 86 percent / iPr2 NEt / CH2 Cl2 / 12 h / 25 °C
17.1: 88 percent / HF*pyridine / tetrahydrofuran / 12 h / 25 °C
18.1: 83 percent / CF3 COOH / CH2 Cl2 / 3 h / 0 °C
19.1: Et3 N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 25 °C
19.2: 59 percent / DMAP / tetrahydrofuran; toluene / 12 h / 25 °C
20.1: hydroquinone; nBu3 SnH / Mo(CO)3(tBuNC)3 / tetrahydrofuran / 12 h / 55 °C
20.2: 54 percent / I2 / CH2 Cl2 / 25 °C
21.1: 90 percent / CuI / Pd(PPh3 )4 / toluene / 8 h / 80 °C
22.1: 69 percent / Me2 BBr / CH2 Cl2 / 2 h / -78 °C
23.1: 85 percent / TEMPO; TCCA / CH2 Cl2 / 1 h / 25 °C
24.1: NaClO2 ; NaH2 PO4 ; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2 O; tetrahydrofuran / 0.5 h / 25 °C
25.1: NaBH4 ; CeCl3 *7H2 O / methanol / 1 h / 0 °C
With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; cerium(III) chloride; 2-methyl-but-2-ene; dimethylboron bromide; [bis(acetoxy)iodo]benzene; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; hydroquinone; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium(0); Mo(CO)3(CN-t-Bu)3; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 2.1: Dess-Martin oxidation / 12.1: Dess-Martin oxidation / 15.1: Mukaiyama reaction / 19.1: Yamaguchi reaction / 25.1: Luche reaction;

7184-60-3 Upstream products

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    631919-63-6

    (1'R,1S,2S,2'R,8R,9S,11R,13S,15S,16S)-2-(7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentane-1'-carboxylic acid 2-trimethylsilanyl-ethyl ester

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    768395-41-1

    (1R,2R)-2-((4E,6Z)-(2S,9S,11R,13S,15S,16S)-7-Cyano-16-hydroxy-9,11,13,15-tetramethyl-8,18-dioxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecarboxylic acid

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    C42 H66 O6 SiNCOCF3

7184-60-3 Downstream products

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    C35 H49 NO6

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    C37 H52 N2 O8

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