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【结 构 式】 
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【分子编号】49284 【品名】(1S,3S,7S,10R,11R,12S,16R)-7-[[tert-butyl(dimethyl)silyl]oxy]-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-5,9-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-11-yl 2,2,2-trichloroethyl carbonate 【CA登记号】 |
【 分 子 式 】C36H56Cl3NO8SSi 【 分 子 量 】797.35218 【元素组成】C 54.23% H 7.08% Cl 13.34% N 1.76% O 16.05% S 4.02% Si 3.52% |
合成路线1
该中间体在本合成路线中的序号：(XXX)The oxidation of the aldehyde group of (XXVIII) with NaClO2 gives the hydroxyacid (XXIX), which is submitted to a Yamaguchi cyclization by means of 2,4,6-trichlorobenzoyl chloride to yield the macrolactone (XXX). Elimination of the Troc protecting group of (XXX) with Zn and NH4Cl affords the silylated precursor (XXXI), which is finally treated with HF and pyridine to provide the target epothilone B.
| 【1】 Martin, H.J.; et al.; How stable are epoxides? A novel synthesis of epothilone B. Angew Chem. Int Ed Engl 2000, 39, 3, 581. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXVIII) | 49282 | (1R,2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxy]-1-((1S)-4-[(2R,3S)-3-[(2S,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2-methyloxiranyl]-1-methylbutyl)-2,4,4-trimethyl-3,7-dioxoheptyl 2,2,2-trichloroethyl carbonate | C36H58Cl3NO8SSi | 详情 | 详情 | |
| (XXIX) | 49283 | C37H61Cl3NO9SSi | 详情 | 详情 | ||
| (XXX) | 49284 | (1S,3S,7S,10R,11R,12S,16R)-7-[[tert-butyl(dimethyl)silyl]oxy]-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-5,9-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-11-yl 2,2,2-trichloroethyl carbonate | C36H56Cl3NO8SSi | 详情 | 详情 | |
| (XXXI) | 49285 | (1S,3S,7S,10R,11R,12S,16R)-7-[[tert-butyl(dimethyl)silyl]oxy]-11-hydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione | C33H55NO6SSi | 详情 | 详情 |