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【结 构 式】 
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【分子编号】44503 【品名】(4S,7R,8S,9S,16S)-8-(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxa-13-cyclohexadecene-2,6-dione 【CA登记号】 |
【 分 子 式 】C39H59NO5SSi 【 分 子 量 】682.0527 【元素组成】C 68.68% H 8.72% N 2.05% O 11.73% S 4.7% Si 4.12% |
合成路线1
该中间体在本合成路线中的序号：(XXXVII)The Yamaguchi macrolactonization of (XXXVI) by means of 2,4,6-trichlorobenzoyl chloride and TEA in THF gives the macrolactone (XXXVII), which is debenzylated with DDQ, yielding (XXXVIII) and desilylated with TFA to afford the dihydroxylactone (XXXIX). Finally, this compound is epoxidated by means of H2O2 and acetonitrile in methanol/water.
| 【1】 Panek, J.S.; Zhu, B.; Total synthesis of apothilone A. Org Lett 2000, 2, 17, 2575. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXXVI) | 44502 | (3S,6R,7S,8S,12Z,15S,16E)-7-(benzyloxy)-3-[[tert-butyl(dimethyl)silyl]oxy]-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoic acid | C39H61NO6SSi | 详情 | 详情 | |
| (XXXVII) | 44503 | (4S,7R,8S,9S,16S)-8-(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxa-13-cyclohexadecene-2,6-dione | C39H59NO5SSi | 详情 | 详情 | |
| (XXXVIII) | 43176 | (4S,7R,8S,9S,16S)-4-[[tert-butyl(dimethyl)silyl]oxy]-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxa-13-cyclohexadecene-2,6-dione | C32H53NO5SSi | 详情 | 详情 | |
| (XXXIX) | 44447 | (4S,7R,8S,9S,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxa-13-cyclohexadecene-2,6-dione | C26H39NO5S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XXXVII)The Yamauchi macrolactonization of (XXXVI) by means of 2,4,6-trichlorobenzoyl chloride and TEA in THF gives the macrolactone (XXXVII), which is debenzylated with DDQ, yielding (XXXVIII), finally desilylated with TFA to afford the target epothilone C.
| 【1】 Panek, J.S.; Zhu, B.; Total synthesis of apothilone A. Org Lett 2000, 2, 17, 2575. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXXVI) | 44502 | (3S,6R,7S,8S,12Z,15S,16E)-7-(benzyloxy)-3-[[tert-butyl(dimethyl)silyl]oxy]-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoic acid | C39H61NO6SSi | 详情 | 详情 | |
| (XXXVII) | 44503 | (4S,7R,8S,9S,16S)-8-(benzyloxy)-4-[[tert-butyl(dimethyl)silyl]oxy]-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxa-13-cyclohexadecene-2,6-dione | C39H59NO5SSi | 详情 | 详情 | |
| (XXXVIII) | 43176 | (4S,7R,8S,9S,16S)-4-[[tert-butyl(dimethyl)silyl]oxy]-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxa-13-cyclohexadecene-2,6-dione | C32H53NO5SSi | 详情 | 详情 |