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【结 构 式】

【分子编号】26251

【品名】(4S,7R,8S,9S,16S)-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-2,6-dioxo-4-[(triethylsilyl)oxy]oxa-13-cyclohexadecen-8-yl 2,2,2-trichloroethyl carbonate

【CA登记号】

【 分 子 式 】C36H56Cl3NO7SSi

【 分 子 量 】781.35278

【元素组成】C 55.34% H 7.22% Cl 13.61% N 1.79% O 14.33% S 4.1% Si 3.59%

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:(XIII)

Further treatment of (X) with Et3SiOTf and 2,6-lutidine protected both 3- and 15-hydroxyl groups as the triethylsilyl ethers and cleaved the tert-butyl ester to yield carboxylic acid (XI). The bis(triethylsilyl)-protected diol (XI) was selectively hydrolyzed to the required 15-hydroxy acid (XII) upon treatment with cold 0.12 M HCl in MeOH. Macrolactonization of (XII) was then performed by means of 2,4,6-trichlorobenzoyl chloride, Et3N and DMAP yielding (XIII). Removal of the trichloroethoxycarbonyl protecting group from the resulting lactone (XIII) employing SmI2 and a catalytic amount of NiI2 in THF at -78 C yielded (XIV). Finally, desilylation of (XIV) with HF-pyridine afforded the target compound.

1 Harris, C.R.; et al.; New chemical synthesis of the promising cancer chemotherapeutic agent 12,13-desoxyepothilone B: Discovery of a surprising long-range effect on the diastereoselectivity of an aldol condensation. J Am Chem Soc 1999, 121, 30, 7050.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(X) 26248 tert-butyl (3S,6R,7S,8S,12Z,15S,16E)-3,15-dihydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-12,16-heptadecadienoate C34H52Cl3NO8S 详情 详情
(XI) 26249 (3S,6R,7S,8S,12Z,15S,16E)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-3,15-bis[(triethylsilyl)oxy]-12,16-heptadecadienoic acid C42H72Cl3NO8SSi2 详情 详情
(XII) 26250 (3S,6R,7S,8S,12Z,15S,16E)-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-3-[(triethylsilyl)oxy]-12,16-heptadecadienoic acid C36H58Cl3NO8SSi 详情 详情
(XIII) 26251 (4S,7R,8S,9S,16S)-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-2,6-dioxo-4-[(triethylsilyl)oxy]oxa-13-cyclohexadecen-8-yl 2,2,2-trichloroethyl carbonate C36H56Cl3NO7SSi 详情 详情
(XIV) 26252 (4S,7R,8S,9S,16S)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4-[(triethylsilyl)oxy]oxa-13-cyclohexadecene-2,6-dione C33H55NO5SSi 详情 详情
Extended Information