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【结 构 式】

【分子编号】21885

【品名】(10S,13R)-17-(1,5-dimethyl-4-oxohexyl)-10,13-dimethyl-8,9,10,11,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one

【CA登记号】

【 分 子 式 】C27H38O2

【 分 子 量 】394.59752

【元素组成】C 82.18% H 9.71% O 8.11%

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:(III)

The dehydrogenation of 3beta-hydroxycholest-5-en-24-one with dichlorodicyanobenzoquinone in refluxing dioxane, or of cholest-4-ene-3,24-dione (II) with chloranil in refluxing tert-butyl alcohol gives cholesta-1,4,6-triene-3,24-dione (III), which is epoxidized with 30% H2O2 and NaOH in methanol-dioxane-THF yielding 1 alpha,2alpha-epoxycholesta-4,6-diene-3,24-dione (IV). The reduction of (IV) with Li in liquid NH3 affords 1alpha,3beta,24-trihydroxycholest-5-ene (V), which is benzoylated with benzoyl chloride in pyridine and submitted to column chromatography on silica gel to give 1alpha,3beta,24R-tribenzoyloxycholest-5-ene (VI). The dehydrogenation of (VI) with dibromodimethylhydantoin of N-bromosuccinimide yields lalpha,3beta,24R-trihydroxy-cholesta-5,7-diene (VII), which is finally submitted to irradiation with a medium-pressure Hg lamp in ether.

1 Ikekawa, N.; Koizumi, N.; Morisaki, M.; Synthesis of active forms of vitamin D. Part IX. S. J Chem Soc - Perkins Trans I 1975, 1421.
2 Takeshita, T.; Hashimoto, Y.; Kawashima, H.; Ishimoto, S.; Ikekawa, N.; Morisaki, M. (Teijin Ltd.); 1alpha,24-Dihydroxycholecalciferol derivs. and pro. DE 2526981; US 4022891 .
3 Castaner, J.; Prous, J.; TV-02. Drugs Fut 1988, 13, 2, 133.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 21890 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; 4,5-dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile 84-58-2 C8Cl2N2O2 详情 详情
(B) 21891 2,3,5,6-Tetrachloro-1,4-benzoquinone; 2,3,5,6-Tetrachlorobenzo-1,4-quinone; p-Chloranil 118-75-2 C6Cl4O2 详情 详情
(I) 21883 6-[(3S,10R,13R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-3-heptanone C27H44O2 详情 详情
(II) 21884 (10R,13R)-17-(1,5-dimethyl-4-oxohexyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one C27H42O2 详情 详情
(III) 21885 (10S,13R)-17-(1,5-dimethyl-4-oxohexyl)-10,13-dimethyl-8,9,10,11,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one C27H38O2 详情 详情
(IV) 21886 (2aR,3aR,3bR,5aR)-6-(1,5-dimethyl-4-oxohexyl)-3b,5a-dimethyl-2a,3a,3b,3c,4,5,5a,6,7,8,8a,8b-dodecahydro-2H-cyclopenta[7,8]phenanthro[3,4-b]oxiren-2-one C27H38O3 详情 详情
(V) 21887 (1S,3R,10R,13R)-17-(4-hydroxy-1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-1,3-diol C27H46O3 详情 详情
(VI) 21888 (1S,3R,10R,13R)-1-(benzoyloxy)-17-[(4R)-4-(benzoyloxy)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl benzoate C48H58O6 详情 详情
(VII) 21889 (1S,3R,10R,13R)-17-[(4R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-1,3-diol C27H44O3 详情 详情
(C) 10463 Benzoyl chloride 98-88-4 C7H5ClO 详情 详情
Extended Information