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【结 构 式】

【分子编号】53738

【品名】(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4Z)-4-isopropyl-1-methyl-4-hexenyl]-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

【CA登记号】n/a

【 分 子 式 】C31H50O2

【 分 子 量 】454.7368

【元素组成】C 81.88% H 11.08% O 7.04%

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:(LIV)

In a different synthesis of intermediate (XI), compound (LIV) (prepared by acetylation of fucosterol (LIII)) was subjected to ozonolysis to produce ketone (LV). Protection of the keto group by ketalization yielded (LVI), which was allylically oxidized to the conjugated ketone (LVII). Double bond reduction in (LVII) by lithium in ammonia, followed by stereoselective reduction of resulting ketone with K-Selectride, yielded alcohol (LVIII). Acid-catalyzed hydrolysis of the ethylene ketal group of (LVIII) gave ketone (LIX). This was converted to intermediate (XI) by reduction with Ca(BH4)2 and subsequent silylation of the resulting alcohol.

1 Moriarty, R.M.; Guo, L.; Tuladhar, S.M. (Genaera Corp.); Chemical synthesis of squalamine. WO 9419366 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 53697 (3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate n/a C35H64O4Si 详情 详情
(LIII) 53737 (3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4Z)-4-isopropyl-1-methyl-4-hexenyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol n/a C29H48O 详情 详情
(LIV) 53738 (3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4Z)-4-isopropyl-1-methyl-4-hexenyl]-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 n/a C31H50O2 详情 详情
(LV) 53712 (3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethyl-4-oxohexyl]-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 n/a C29H46O3 详情 详情
(LVI) 53739 (3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-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 n/a C31H50O4 详情 详情
(LVII) 53740 (3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-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 n/a C31H48O5 详情 详情
(LVIII) 53741 (3S,5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate n/a C31H52O5 详情 详情
(LIX) 53742 (3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R)-1,5-dimethyl-4-oxohexyl]-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate n/a C29H48O4 详情 详情
Extended Information