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【结 构 式】 
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【分子编号】29792 【品名】(8S,13S,14S)-3,17-bis(benzyloxy)-13-methyl-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene; benzyl (8S,13S,14S)-17-(benzyloxy)-13-methyl-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-3-yl ether 【CA登记号】 |
【 分 子 式 】C32H34O2 【 分 子 量 】450.62076 【元素组成】C 85.29% H 7.61% O 7.1% |
合成路线1
该中间体在本合成路线中的序号：(II)RU-16117 is synthesized from D9(11)-estradiol (I). After protecting the hydroxyl groups by the formation of a benzyl ether (II), the double bond is hydrated by hydroboration, followed by oxidation with hydrogen peroxide in alkali. The alcohol thus formed (III) is treated with sodium hydride and then methyliodide (IV). After deprotection of the 3 and 17 hydroxyl groups (V), the C-17 hydroxyl is oxidized to a ketone by chromic oxidation (VI) and the 17-alpha-ethynyl group is introduced directly with potassium acetylide.
| 【1】 Bouton, M.M.; Raynaud, J.P.; Azadian-Boulanger, G.; Bucourt, .; Pierdet, A.; Torelli, V.; Nédélec, L.; Dérivés 11-alpha-méthoxylés de l'estradiol: Activité anti-estrogène du 11-alpha-méthoxy éthynyl estradiol: RU-16117. Eur J Med Chem 1978, 13, 4, 313-319. |
| 【2】 Précigous, G.; Analyse Radiocristallographique de Molécules Oestrogènes et Androgènes et Etude de leur Affinité et de leur Spécificité. Ph. D. Thesis, Univ. Bordeaux I 1978. |
| 【3】 Azadian-Boulanger, G.; Raynaud, J.P.; RU-16117. Drugs Fut 1985, 10, 5, 926. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 | |
| 23634 | acetylene | 74-86-2 | C2H2 | 详情 | 详情 | |
| (I) | 29791 | (8S,13S,14S)-13-methyl-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol | C18H22O2 | 详情 | 详情 | |
| (II) | 29792 | (8S,13S,14S)-3,17-bis(benzyloxy)-13-methyl-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene; benzyl (8S,13S,14S)-17-(benzyloxy)-13-methyl-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-3-yl ether | C32H34O2 | 详情 | 详情 | |
| (III) | 29793 | (8S,9S,11R,13S,14S)-3,17-bis(benzyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-11-ol | C32H36O3 | 详情 | 详情 | |
| (IV) | 29794 | (8S,9S,11R,13S,14S)-3,17-bis(benzyloxy)-11-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene; benzyl (8S,9S,11R,13S,14S)-17-(benzyloxy)-11-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ether | C33H38O3 | 详情 | 详情 | |
| (V) | 29795 | (8S,9S,11R,13S,14S)-11-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol | C19H26O3 | 详情 | 详情 | |
| (VI) | 29796 | (8S,9S,11R,13S,14S)-3-hydroxy-11-methoxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one | C19H24O3 | 详情 | 详情 |