(3S,5S,7R,8R,9S,10S,13S,14S,17S)-7-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】53756

【品名】(3S,5S,7R,8R,9S,10S,13S,14S,17S)-7-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

【CA登记号】n/a

【分子式】C₂₅H₄₀O₅

【分子量】420.5896

【元素组成】C 71.39% H 9.59% O 19.02%

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：(LXXVI)

In another synthetic route from pregnenolone acetate (LXXIII), its ketalization to (LXXIV) followed by allylic oxidation led to enone (LXXV). Sequential reduction of (LXXV) with lithium in liquid ammonia and then with K-Selectride gave alcohol (LXXVI), which was further protected as the methoxymethyl derivative (LXXVII). Selective deprotection of the C-20 ketal of (LXXVII) yielded ketone (LXXVIII). Ylide (LXXX) was prepared by condensation of bromide (LXXIX) with triphenylphosphine, followed by deprotonation with n-BuLi. Wittig condensation of ketone (LXXVIII) with phosphorane (LXXX) furnished olefin (LXXXI). Then, double-bond hydrogenation and deprotection of the 7-hydroxyl group of (LXXXI) gave rise to the intermediate (XI).

参考文献中间体

合成目标

【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
(LXXIII)	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
(LXXIV)	53754	(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	n/a	C₂₅H₃₈O₄	详情	详情
(LXXV)	53755	(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-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	C₂₅H₃₆O₅	详情	详情
(LXXVI)	53756	(3S,5S,7R,8R,9S,10S,13S,14S,17S)-7-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	n/a	C₂₅H₄₀O₅	详情	详情
(LXXVII)	53757	(3S,5S,7R,8R,9S,10S,13S,14S,17S)-7-(methoxymethoxy)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	n/a	C₂₇H₄₄O₆	详情	详情
(LXXVIII)	53758	(3S,5S,7R,8R,9S,10S,13S,14S,17S)-17-acetyl-7-(methoxymethoxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	n/a	C₂₅H₄₀O₅	详情	详情
(LXXIX)	53759	1-(2-bromoethyl)-2-methylpropyl tert-butyl(dimethyl)silyl ether; [1-(2-bromoethyl)-2-methylpropoxy](tert-butyl)dimethylsilane	n/a	C₁₂H₂₇BrOSi	详情	详情
(LXXX)	53760	(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methylpentylidene)(triphenyl)phosphorane; tert-butyl(dimethyl)silyl 2-methyl-1-[2-(triphenylphosphoranylidene)ethyl]propyl ether	n/a	C₃₀H₄₁OPSi	详情	详情
(LXXXI)	53761	(3S,5S,7R,8R,9S,10S,13S,14S,17R)-17-((Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethyl-1-hexenyl)-7-(methoxymethoxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	n/a	C₃₇H₆₆O₅Si	详情	详情

Extended Information