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【结 构 式】

【分子编号】52589

【品名】3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-7-({[(2,2,2-trichloroethyl)oxy]carbonyl}oxy)-12,16-heptadecadienoic acid

【CA登记号】

【 分 子 式 】C36H58Cl3NO8SSi

【 分 子 量 】799.36806

【元素组成】C 54.09% H 7.31% Cl 13.31% N 1.75% O 16.01% S 4.01% Si 3.51%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XXb)

The treatment of (XVIII) with Troc-Cl and pyridine gives fully protected (XIX) as the same diastereomeric mixture, which is selectively deprotected at the Sem group with TFA in dichloromethane to yield the corresponding mixture of hydroxyacids (XX). The macrolactonization of (XX) by the Yamaguchi method (2,4,6-trichlrobenzoyl chloride, TEA and DMAP in toluene) gives the diastereomeric mixture of lactones (XXI), which are readily separated by flash column chromatography. The desired diastereomer (XXII) is desilylated with HF and pyridine, yielding the hydroxylactone (XXIII), which is treated with Zn and NH4Cl in refluxing aqueous methanol to eliminate the Troc protecting group and provide the unprotected precursor (XXIV). Finally, this compound is epoxidated with methyl(trifluoromethyl)dioxirane (MTFDO) to afford the target epothilone B.

1 Valluri, M.; et al.; Total synthesis of epothilone B. Org Lett 2001, 3, 23, 3607.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVIIIa) 52584 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-15-[({[2-(trimethyl-lambda~4~-sulfanyl)ethyl]oxy}methyl)oxy]-12,16-heptadecadienoic acid C39H71NO7S2Si 详情 详情
(XVIIIb) 52585 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-15-[({[2-(trimethyl-lambda~4~-sulfanyl)ethyl]oxy}methyl)oxy]-12,16-heptadecadienoic acid C39H71NO7S2Si 详情 详情
(XIXa) 52586 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-7-({[(2,2,2-trichloroethyl)oxy]carbonyl}oxy)-15-[({[2-(trimethyl-lambda~4~-sulfanyl)ethyl]oxy}methyl)oxy]-12,16-heptadecadienoic acid C42H72Cl3NO9S2Si 详情 详情
(XIXb) 52587 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-7-({[(2,2,2-trichloroethyl)oxy]carbonyl}oxy)-15-[({[2-(trimethyl-lambda~4~-sulfanyl)ethyl]oxy}methyl)oxy]-12,16-heptadecadienoic acid C42H72Cl3NO9S2Si 详情 详情
(XXa) 52588 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-7-({[(2,2,2-trichloroethyl)oxy]carbonyl}oxy)-12,16-heptadecadienoic acid C36H58Cl3NO8SSi 详情 详情
(XXb) 52589 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-7-({[(2,2,2-trichloroethyl)oxy]carbonyl}oxy)-12,16-heptadecadienoic acid C36H58Cl3NO8SSi 详情 详情
(XXIa),(XXII) 52590 4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-2,6-dioxooxa-13-cyclohexadecen-8-yl 2,2,2-trichloroethyl carbonate C36H56Cl3NO7SSi 详情 详情
(XXIb) 52591 4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-2,6-dioxooxa-13-cyclohexadecen-8-yl 2,2,2-trichloroethyl carbonate C36H56Cl3NO7SSi 详情 详情
(XXIII) 52592 4-hydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-2,6-dioxooxa-13-cyclohexadecen-8-yl 2,2,2-trichloroethyl carbonate C30H42Cl3NO7S 详情 详情
(XXIV) 40837 (4S,7R,8S,9S,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxa-13-cyclohexadecene-2,6-dione C27H41NO5S 详情 详情
Extended Information