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【结 构 式】 
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【分子编号】49365 【品名】(4S,7R,8S,9S,16S)-8-hydroxy-16-[(E)-2-[2-(hydroxymethyl)-1,3-thiazol-4-yl]-1-methylethenyl]-5,5,7,9,13-pentamethyl-4-[(triethylsilyl)oxy]oxa-13-cyclohexadecene-2,6-dione 【CA登记号】 |
【 分 子 式 】C33H55NO6SSi 【 分 子 量 】621.95434 【元素组成】C 63.73% H 8.91% N 2.25% O 15.43% S 5.16% Si 4.52% |
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：(XXIV)The macrocyclization of (XXII) under Yamaguchi conditions (trichlorobenzoyl chloride, TEA and DMAP) in toluene gives the macrolactone (XXIII), which is treated with Zn and HOAc in THF or with NiI2/SmI2 in the same solvent to eliminate the two Troc protecting groups to yield the monosilylated intermediate (XXIV). Finally, this compound is desilylated by means of HF and pyridine in THF to afford the target 12,13-desoxyepothilone F.
| 【1】 Zhang, X.-G.; Chappell, M.D.; Lee, C.B.; Kuduk, S.D.; Danishefsky, S.J.; Chou, T.-C.; Wang, Z.-G.; Stachel, S.J.; Total synthesis and antitumor activity of 12,13-dexoxyepothilone F: An unexpected solvolysis problem at C15, mediated by remote substitution at C21. J Org Chem 2000, 65, 20, 6525. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXII) | 49363 | (3S,6R,7S,8S,12Z,15S,16E)-15-hydroxy-4,4,6,8,12,16-hexamethyl-5-oxo-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-17-[2-([[(2,2,2-trichloroethoxy)carbonyl]oxy]methyl)-1,3-thiazol-4-yl]-3-[(triethylsilyl)oxy]-12,16-heptadecadienoic acid | C39H59Cl6NO11SSi | 详情 | 详情 | |
| (XXIII) | 49364 | [4-((E)-2-[(2S,9S,10S,11R,14S)-5,9,11,13,13-pentamethyl-12,16-dioxo-10-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-14-[(triethylsilyl)oxy]oxa-4-cyclohexadecen-2-yl]-1-propenyl)-1,3-thiazol-2-yl]methyl 2,2,2-trichloroethyl carbonate | C39H57Cl6NO10SSi | 详情 | 详情 | |
| (XXIV) | 49365 | (4S,7R,8S,9S,16S)-8-hydroxy-16-[(E)-2-[2-(hydroxymethyl)-1,3-thiazol-4-yl]-1-methylethenyl]-5,5,7,9,13-pentamethyl-4-[(triethylsilyl)oxy]oxa-13-cyclohexadecene-2,6-dione | C33H55NO6SSi | 详情 | 详情 |
Extended Information