• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】35181

【品名】3-[(3S,3aS,5aS,6R,9S,9aS,9bS)-3-[(1R)-1-hydroxyethyl]-3a,6,9-trimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalen-6-yl]propionic acid

【CA登记号】

【 分 子 式 】C21H34O4

【 分 子 量 】350.49856

【元素组成】C 71.96% H 9.78% O 18.26%

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:(IX)

Pregnenolone acetate (I) was reduced with NaBH4 to give alcohol (II), which was subsequently protected as the silyl ether (III) by means of tert-butyl dimethylsilyl chloride and imidazole. Allylic oxidation of (III) with tert-butyl hydroperoxide and chromium hexacarbonyl produced the unsaturated ketone (IV). Addition of methylmagnesium chloride to (IV), with concomitant cleavage of the acetate ester, yielded diol (V), and further Oppenauer oxidation using cyclohexanone and aluminum triisopropoxide generated dienone (VI). Selective reduction of one double bond of (VI) to give enone (VII) was achieved by transfer hydrogenation with cyclohexene and Pd/C. Oxidative cleavage of the A ring of (VII) with NaIO4 and KMnO4 to give (VIII), followed by HF-promoted desilylation furnished the 7beta-methylpregnane seco-acid (IX). This was cyclized with 2,4-dimethoxybenzyl amine (X) affording the azasteroid (XI).

1 Harris, G.S.; Tolman, R.L.; Ellsworth, K.P.; Rasmusson, G.H.; Chang, B.C.; Patel, G.F.; Bakshi, R.K.; 3-Oxo-4aza-5alpha-7beta-methylpregnan-20-ethers as inhibitors of human type 1 5alpha-reductase: Synthesis and structure-activity relationship. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 226.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 35173 (3S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 1778-02-5 C23H34O3 详情 详情
(II) 35174 (3S,8S,9S,10R,13S,14S,17S)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 14553-79-8 C23H36O3 详情 详情
(III) 35175 (3S,8S,9S,10R,13S,14S,17S)-17-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate C29H50O3Si 详情 详情
(IV) 35176 (3S,8S,9S,10R,13S,14S,17S)-17-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-10,13-dimethyl-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate C29H48O4Si 详情 详情
(V) 35177 (3S,8S,9S,10R,13S,14S,17S)-17-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-7,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol C28H50O3Si 详情 详情
(VI) 35178 (8S,9S,10R,13S,14S,17S)-17-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-7,10,13-trimethyl-1,2,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one C28H46O2Si 详情 详情
(VII) 35179 (7S,8S,9S,10R,13S,14S,17S)-17-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-7,10,13-trimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one C28H48O2Si 详情 详情
(VIII) 35180 3-[(3S,3aS,5aS,6R,9S,9aS,9bS)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-3a,6,9-trimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalen-6-yl]propionic acid C27H48O4Si 详情 详情
(IX) 35181 3-[(3S,3aS,5aS,6R,9S,9aS,9bS)-3-[(1R)-1-hydroxyethyl]-3a,6,9-trimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalen-6-yl]propionic acid C21H34O4 详情 详情
(X) 32115 (2,4-dimethoxyphenyl)methanamine; 2,4-dimethoxybenzylamine 20781-21-9 C9H13NO2 详情 详情
(XI) 35182 (4aR,4bS,6aS,7S,9aS,9bS,10R)-1-(2,4-dimethoxybenzyl)-7-[(1R)-1-hydroxyethyl]-4a,6a,10-trimethyl-1,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one C30H43NO4 详情 详情
Extended Information