(5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】53780

【品名】(5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate

【CA登记号】

【分子式】C₃₁H₅₀O₅

【分子量】502.735

【元素组成】C 74.06% H 10.02% O 15.91%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(CII)

Birch reduction of enone (XCVII), followed by reduction of the saturated ketone (XCVIII) with K-Selectride, provided alcohol (XCIX). Acetylation of (IC) gave the triacetate (C). Selective hydrolysis of the C-3 acetate group of (C) with NaCN in MeOH yielded alcohol (CI), which was oxidized to ketone (CII) by using the Jones reagent.

参考文献中间体

合成目标

【1】 Moriarty, R.M.; et al.; Stereoselective synthesis of squalamine dessulfate. Tetrahedron Lett 1995, 36, 29, 5139.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IC)	53777	(3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	C₃₁H₅₂O₅	详情	详情
(CI)	53779	(3S,5R,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate	C₃₁H₅₂O₅	详情	详情
(CII)	53780	(5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate	C₃₁H₅₀O₅	详情	详情
(XCVII)	53775	(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-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	C₃₁H₄₈O₅	详情	详情
(XCVIII)	53776	(3S,5R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	C₃₁H₅₀O₅	详情	详情
(C)	53778	(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-(acetyloxy)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate	C₃₃H₅₄O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(CII)

Reductive amination of ketone (CII) with the deprotected spermidine (XL) in the presence of NaBH3CN provided the triamino derivative (CIII). The Boc protecting groups of (CIII) were then removed by acidic treatment to furnish the target precursor (CIV).

参考文献中间体

合成目标

【1】 Moriarty, R.M.; et al.; Stereoselective synthesis of squalamine dessulfate. Tetrahedron Lett 1995, 36, 29, 5139.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(CII)	53780	(5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate		C₃₁H₅₀O₅	详情	详情
(CIII)	53781	(1R,4R)-4-((3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(acetyloxy)-3-{[3-((tert-butoxycarbonyl){4-[(tert-butoxycarbonyl)amino]butyl}amino)propyl]amino}-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-isopropylpentyl acetate		C₄₈H₈₅N₃O₈	详情	详情
(CIV)	53782	(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-({3-[(4-aminobutyl)amino]propyl}amino)-17-[(1R,4R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-ol		C₃₄H₆₅N₃O₂	详情	详情
(XL)	53724	tert-butyl 3-aminopropyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate	n/a	C₁₇H₃₅N₃O₄	详情	详情

Extended Information