(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-[(2,2,2-trichloroethoxycarbonyl)oxy]-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-[(2,2,2-trichloroethoxycarbonyl)oxy]-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.:823789-87-3
Molecular Formula:C₄₂H₇₂Cl₃NO₉SSi₂
Molecular Weight:929.631
Hs Code.:

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

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

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

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Technology Process of (3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-[(2,2,2-trichloroethoxycarbonyl)oxy]-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-[(2,2,2-trichloroethoxycarbonyl)oxy]-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:

: 6436-59-5
ethyl 2-methylthiazole-4-carboxylate

: 823789-87-3
(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-[(2,2,2-trichloroethoxycarbonyl)oxy]-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

Guidance literature:: Multi-step reaction with 10 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

8.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

9.1: CH₂Cl₂ / 5 h / 20 °C

10.1: 0.67 g / acetic acid / tetrahydrofuran; H₂O / 3 h / 0 °C

With pyridine; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; carbon tetrabromide; dimethylsulfide borane complex; (1R)-(+)-pinene; acetic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; 4.2: Wadsworth-Horner-Emmons reaction / 6.1: Swern oxidation;
DOI:10.1021/jo048742o

Reference yield:

: 823789-87-3
(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-[(2,2,2-trichloroethoxycarbonyl)oxy]-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

: 152044-54-7
epothilone B

Guidance literature:: Multi-step reaction with 5 steps

1.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C

2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C

2.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C

3.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating

4.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C

5.1: 30 percent / m-CPBA / CHCl₃ / 5 h / -10 - 0 °C

With nitromethane; n-butanethiol; 2,4,6-trichlorobenzoyl chloride; ammonium chloride; pyridine hydrogenfluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; magnesium bromide; zinc; In tetrahydrofuran; methanol; diethyl ether; chloroform; 2.2: Yamaguchi macrolactonization;
DOI:10.1021/jo048742o

Reference yield:

: 823789-87-3
(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-[(2,2,2-trichloroethoxycarbonyl)oxy]-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

: 189453-10-9
epothilone D

Guidance literature:: Multi-step reaction with 4 steps

1.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C

2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C

2.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C

3.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating

4.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C

With nitromethane; n-butanethiol; 2,4,6-trichlorobenzoyl chloride; ammonium chloride; pyridine hydrogenfluoride; triethylamine; magnesium bromide; zinc; In tetrahydrofuran; methanol; diethyl ether; 2.2: Yamaguchi macrolactonization;
DOI:10.1021/jo048742o