(8R,9S,13S,14S,17S)-2-acetyl-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】59432

【品名】(8R,9S,13S,14S,17S)-2-acetyl-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate

【CA登记号】

【分子式】C₂₂H₂₈O₄

【分子量】356.46192

【元素组成】C 74.13% H 7.92% O 17.95%

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：(XXIX)

In a related method starting from estradiol 3-methyl ether 17-acetate (XXVII), Friedel-Crafts acetylation in the presence of AlCl3 gave ketone (XXVIII). The methyl ether group was then cleaved employing HBr in HOAc to afford phenol (XXIX). Protection of phenol (XXIX) as the benzyl ether, followed by reacetylation of the 17-hydroxyl group furnished (XXX), which was further subjected to Baeyer-Villiger oxidation to provide diacetate (XXXI). Hydrolysis of (XXXI) under basic conditions gave diol (XXXII). Methylation of (XXXII) by means of diazomethane provided the 2-methoxy derivative (XXXIII). The O-benzyl protecting group was finally removed by catalytic hydrogenolisis.

参考文献中间体

合成目标

【1】 Nambara, T.; et al.; Studies on steroid conjugates. III. New syntheses of 2-methoxyestrogens. Chem Pharm Bull 1970, 18, 3, 474.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXVII)	59430	(8R,9S,13S,14S,17S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate	C₂₁H₂₈O₃	详情	详情
(XXVIII)	59431	(8R,9S,13S,14S,17S)-2-acetyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate	C₂₃H₃₀O₄	详情	详情
(XXIX)	59432	(8R,9S,13S,14S,17S)-2-acetyl-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate	C₂₂H₂₈O₄	详情	详情
(XXX)	59433	(8R,9S,13S,14S,17S)-2-acetyl-3-(benzyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate	C₂₉H₃₄O₄	详情	详情
(XXXI)	59434	(8R,9S,13S,14S,17S)-17-(acetyloxy)-3-(benzyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-yl acetate	C₂₉H₃₄O₅	详情	详情
(XXXII)	59435	(8R,9S,13S,14S,17S)-3-(benzyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2,17-diol	C₂₅H₃₀O₃	详情	详情
(XXXIII)	59436	(8R,9S,13S,14S,17S)-3-(benzyloxy)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol	C₂₆H₃₂O₃	详情	详情

Extended Information