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【结 构 式】 
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【分子编号】32588 【品名】(3S,8R,9S,10R,13S,14S)-17-(5-isoxazolyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol 【CA登记号】 |
【 分 子 式 】C22H29NO2 【 分 子 量 】339.4778 【元素组成】C 77.84% H 8.61% N 4.13% O 9.43% |
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：(III)Claisen condensation of 3-beta-acetyloxypregna-5,16-dien-20-one (I) with ethyl formate in the presence of NaOMe in pyridine, with simultaneous deacetylation, provided the corresponding 21-formyl derivative (II). Subsequent treatment of (II) with hydroxylamine yielded isoxazole (III) as the only regioisomer. Finally, Oppenauer oxidation of (III) with cyclohexanone and aluminum isopropoxide gave rise to the target alpha,beta-unsaturated ketone.
| 【1】 Ling, Y.; et al.; 17-Imidazolyl, pyrazolyl, and isoxazolyl androstene derivatives, novel steroidal inhibitors of human cytochrome C17,20-lyase (P45017alpha). J Med Chem 1997, 40, 20, 3297. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 16602 | ethyl formate | 109-94-4 | C3H6O2 | 详情 | 详情 | |
| (I) | 32586 | (3S,8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | 979-02-2 | C23H32O3 | 详情 | 详情 |
| (II) | 32587 | (Z)-3-hydroxy-1-[(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-propen-1-one | C22H30O3 | 详情 | 详情 | |
| (III) | 32588 | (3S,8R,9S,10R,13S,14S)-17-(5-isoxazolyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | C22H29NO2 | 详情 | 详情 |
Extended Information