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【结 构 式】 
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【分子编号】59976 【品名】(8S,9R,10S,13S,14S,17R)-17-acetyl-9,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one 【CA登记号】 |
【 分 子 式 】C21H30O4 【 分 子 量 】346.4668 【元素组成】C 72.8% H 8.73% O 18.47% |
合成路线1
该中间体在本合成路线中的序号：(VI)Androstenedione (II) was converted to the C-17 cyanohydrin (III) by treatment with either KCN and AcOH or with acetone cyanohydrin and NaOH. Ketalization of the remaining 3-keto group with ethylene glycol and trimethyl orthoformate led to (IV). The C-17 hydroxyl was then protected by formation of the acetaldehyde mixed ketal (V) by treatment with butyl vinyl ether. Addition of methyllithium to the cyano group, followed by acidic ketal hydrolysis furnished the pregnenedione (VI). Subsequent iodination of (VI) by means of iodine and calcium oxide gave iodo ketone (VII), which was further displaced by potassium acetate yielding the C-21 acetate ester (VIII). Finally, dehydration of the C-17 alcohol employing 70% aqueous sulfuric acid produced the title compound.
| 【1】 Batist, J.N.M.; Marx, A.F.; Van Zoest, W.J.; Kapur, J.C. (Gist-Brocades NV); 9-alpha-Hydroxy steroids and process for their preparation. EP 0263569; JP 1989500907; WO 8802753 . |
| 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) | 23199 | 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether | 67-64-1 | C3H6O | 详情 | 详情 |
| (A) | 59983 | 1-butoxyethylene; butyl vinyl ether | 111-34-2 | C6H12O | 详情 | 详情 |
| (II) | 28065 | (8S,9R,10S,13S,14S)-9-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione | C19H26O3 | 详情 | 详情 | |
| (III) | 59973 | (8S,9R,10S,13S,14S,17R)-9,17-dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonitrile | C20H27NO3 | 详情 | 详情 | |
| (IV) | 59974 | C22H31NO4 | 详情 | 详情 | ||
| (V) | 59975 | C28H43NO5 | 详情 | 详情 | ||
| (VI) | 59976 | (8S,9R,10S,13S,14S,17R)-17-acetyl-9,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one | C21H30O4 | 详情 | 详情 | |
| (VII) | 59977 | (8S,9R,10S,13S,14S,17R)-9,17-dihydroxy-17-(2-iodoacetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one | C21H29IO4 | 详情 | 详情 | |
| (VIII) | 59978 | 2-[(8S,9R,10S,13S,14S,17R)-9,17-dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate | C23H32O6 | 详情 | 详情 |