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【结 构 式】 
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【分子编号】32637 【品名】3-Methoxyspiro[estra-2,5(10)-diene-17(S),2'-oxirane] 【CA登记号】 |
【 分 子 式 】C20H28O2 【 分 子 量 】300.44112 【元素组成】C 79.96% H 9.39% O 10.65% |
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：(II)1,4-Dihydroestronemethylether (I) was reacted with dimethylsulfonium-methylide (A) in a highly stereoselective manner to give the oxirane (II), which formed the cyanomethyl compound (III) by the addition of sodium cyanide. (III) was hydrolyzed with oxalic acid (B) in methanol and the product (IV) treated with pyridine perbromide hydrobromide to the dibromoketone, which yielded STS-557 after dehydrobromination.
| 【1】 Cook, C.E.; et al.; Synthesis and reactions of oxiranes obtained from 3- and 17-keto steroids. J Org Chem 1968, 33, 2789. |
| 【2】 Hubner, M.; et al.; Ein vereinfachtes Verfahren zur Darstellung von Steroid-Spirooxiranen. J Prakt Chem 1972, 314, 667. |
| 【3】 Ponsold, K.; et al.; Prostagene vom Typ 17alpha-CH2X-substituierter 19-Nortestossteronderivate. Pharmazie 1978, 33, 792. |
| 【4】 Perelman, M.; et al.; A new class of active steroids: the 19-nor-delta(4,9)-3-ketosteroids. J Am Chem Soc 1960, 82, 2402. |
| 【5】 Unterhalt, B.; STS-557. Drugs Fut 1980, 5, 6, 311. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 15713 | Oxalic acid | 144-62-7 | C2H2O4 | 详情 | 详情 |
| (A) | 16180 | Dimethyl(methylene)-lambda(4)-sulfane; Dimethylsulfonium-methylide | C3H8S | 详情 | 详情 | |
| (I) | 32635 | 1,4-Dihydroestronemethylether; (8R,9S,13S,14S)-3-methoxy-13-methyl-1,4,6,7,8,9,11,12,13,14,15,16-dodecahydro-17H-cyclopenta[a]phenanthren-17-one | C19H26O2 | 详情 | 详情 | |
| (II) | 32637 | 3-Methoxyspiro[estra-2,5(10)-diene-17(S),2'-oxirane] | C20H28O2 | 详情 | 详情 | |
| (III) | 32636 | 2-[(8R,9S,13S,14S,17R)-17-hydroxy-3-methoxy-13-methyl-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]acetonitrile | C21H29NO2 | 详情 | 详情 | |
| (IV) | 32638 | 2-[(8R,9S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-2,3,4,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]acetonitrile | C20H27NO2 | 详情 | 详情 |
Extended Information