(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

Base Information

• Chemical Name: (3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid
• CAS No.: 823789-81-7
• Molecular Formula: C₃₉H₇₁NO₇SSi₂
• Molecular Weight: 754.232
• Mol file: 823789-81-7.mol

Synonyms:(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

Chemical Property of (3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

There total 1 articles about (3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

ethyl 2-methylthiazole-4-carboxylate (6436-59-5) → (3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid (823789-81-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 84 percent / LiAlH₄ / diethyl ether / 3 h / -78 °C

2.1: 85 percent / Ph₃P; CBr₄ / CCl₄ / 3 h / 20 °C

3.1: 86 percent / 3 h / 160 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

5.1: (1R)-(+)-pinene; BH₃*DMS / tetrahydrofuran / 0.5 h / 20 °C

5.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H₂O / 2 h / 20 °C

6.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C

7.2: 59 percent / ZnCl₂ / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; carbon tetrabromide; dimethylsulfide borane complex; (1R)-(+)-pinene; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; 4.2: Wadsworth-Horner-Emmons reaction / 6.1: Swern oxidation;

DOI:10.1021/jo048742o

Reference yield:

(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid (823789-81-7) → epothilone B (152044-54-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

2.1: CH₂Cl₂ / 5 h / 20 °C

3.1: 0.67 g / acetic acid / tetrahydrofuran; H₂O / 3 h / 0 °C

4.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C

5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C

5.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C

6.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating

7.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C

8.1: 30 percent / m-CPBA / CHCl₃ / 5 h / -10 - 0 °C

With pyridine; nitromethane; n-butanethiol; 2,4,6-trichlorobenzoyl chloride; ammonium chloride; pyridine hydrogenfluoride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; magnesium bromide; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; 5.2: Yamaguchi macrolactonization;

DOI:10.1021/jo048742o

Reference yield:

(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid (823789-81-7) → epothilone D (189453-10-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

2.1: CH₂Cl₂ / 5 h / 20 °C

3.1: 0.67 g / acetic acid / tetrahydrofuran; H₂O / 3 h / 0 °C

4.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C

5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C

5.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C

6.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating

7.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C

With pyridine; nitromethane; n-butanethiol; 2,4,6-trichlorobenzoyl chloride; ammonium chloride; pyridine hydrogenfluoride; acetic acid; triethylamine; magnesium bromide; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 5.2: Yamaguchi macrolactonization;

DOI:10.1021/jo048742o

upstream raw materials:

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

epothilone B

epothilone D