(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】53751

【品名】(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

【CA登记号】n/a

【分子式】C₃₁H₅₂O₄

【分子量】488.75148

【元素组成】C 76.18% H 10.72% O 13.09%

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：(LXX)

In a synthetic route starting from dehydroepiandrosterone (LXVI), Wittig reaction of ketone (LXVI) with ethyl triphenylphosphonium bromide (LXVII) and potassium tert-butoxide gave the C-17 ethylidene derivative (LXVIII). Condensation of (LXVIII) with isopropyl vinyl ketone (LXIX) in the presence of dimethylaluminum chloride, followed by catalytic hydrogenation over Pt/C, yielded (LV), which was then converted into ethylene ketal (LVI). Catalytic hydrogenation of (LVI) gave compound (LXX), whose acetate ester was hydrolyzed to afford alcohol (LXXI). Oxidation of (LXXI) by means of chromic acid furnishes ketone (LXXII), from which intermediate (LX) was obtained by introduction of the 7-alpha hydroxyl group by means of microbiological oxidation employing several microorganism strains.

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
(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
(LX)	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
(LXVI)	20083	Prasterone acetate;3b-Hydroxy-5-androstene-17-one acetate；Dehydroisoandrosterone acetate;Dehydroepiandrosterone 3-acetate;Dehydroepiandrosterone acetate;(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	853-23-6	C₂₁H₃₀O₃	详情	详情
(LXVII)	11717	Ethyl(triphenyl)phosphonium bromide; (Ethyl)triphenylphosphonium bromide	1530-32-1	C₂₀H₂₀BrP	详情	详情
(LXVIII)	53749	(3S,8S,9S,10R,13S,14S)-17-[(E)ethylidene]-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	C₂₃H₃₄O₂	详情	详情
(LXIX)	53750	4-methyl-1-penten-3-one	1606-47-9	C₆H₁₀O	详情	详情
(LXX)	53751	(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	n/a	C₃₁H₅₂O₄	详情	详情
(LXXI)	53752	(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol	n/a	C₂₉H₅₀O₃	详情	详情
(LXXII)	53753	(5S,8R,9S,10S,13R,14S,17R)-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one	n/a	C₂₉H₄₈O₃	详情	详情

Extended Information