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【结 构 式】

【分子编号】34389

【品名】(5S,7S,8R,9S,10S,13S,14S,17S)-7,17-dihydroxy-10,13,17-trimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one

【CA登记号】

【 分 子 式 】C20H32O3

【 分 子 量 】320.47228

【元素组成】C 74.96% H 10.06% O 14.98%

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:(VI)

Ketalization of 17alpha-methyltestosterone (I) by means of ethylene glycol and p-toluenesulfonic acid provided the DELTA5(6)-ketal (II), and subsequent allylic oxidation of (II) with CrO3-3,5-dimethylpyrazole complex gave enone (III). Hydrogenation of the olefinic double bond of (III) afforded the saturated ketone (IV), which was reduced employing NaBH4 and CeCl3 to furnish an unseparable mixture of epimeric alcohols (Va-b). After removal of the ethylene ketal of (Va-b) with p-toluenesulfonic acid/acetone, the major 7beta-alcohol (VI) was isolated by flash chromatography. The 7beta-tosylate (VII) was then prepared by reaction of (VI) with p-tosyl chloride in pyridine. Finally, exchange of the tosylate group of (VII) with tetrabutylammonium fluoride yielded the desired 7alpha-fluoride.

1 Labaree, D.C.; et al.; 7alpha-Iodo and 7alpha-fluoro steroids as androgen receptor-mediated imaging agents. J Med Chem 1999, 42, 11, 2021.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
(Va) 34387   C22H36O4 详情 详情
(Vb) 34388   C22H36O4 详情 详情
(I) 34383 (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one 58-18-4 C20H30O2 详情 详情
(II) 34384   C22H34O3 详情 详情
(III) 34385   C22H32O4 详情 详情
(IV) 34386   C22H34O4 详情 详情
(VI) 34389 (5S,7S,8R,9S,10S,13S,14S,17S)-7,17-dihydroxy-10,13,17-trimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one C20H32O3 详情 详情
(VII) 34390 (5S,7S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl 4-methylbenzenesulfonate C27H38O5S 详情 详情
Extended Information