(1R,4R)-4-[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-({3-[(3-cyanopropyl)amino]propyl}amino)-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-isopropylpentyl hydrogen sulfate -Drug Synthesis Database

【结构式】

【分子编号】53801

【品名】(1R,4R)-4-[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-({3-[(3-cyanopropyl)amino]propyl}amino)-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-isopropylpentyl hydrogen sulfate

【CA登记号】n/a

【分子式】C₃₄H₆₁N₃O₅S

【分子量】623.94156

【元素组成】C 65.45% H 9.85% N 6.73% O 12.82% S 5.14%

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：(CXXIII)

Treatment of the OH group of (CXIX) with SO3-pyridine provided sulfate (CXX). The benzoate ester of (CXX) was subsequently hydrolyzed under basic conditions to give (CXXI). Reductive amination of (CXXI) with the cyanodiamine (CXXII) afforded (CXXIII). The cyano group of (CXXIII) was finally reduced to the target amine by catalytic hydrogenation.

参考文献中间体

合成目标

【1】 Zhang, X.; et al.; Synthesis of squalamine utilizing a readily accessible spermidine equivalent. J Org Chem 1998, 63, 23, 8599.
【2】 Kinney, W.A.; Meckler, H.; Zhang, X.; Lee, N.; Jones, S.; Rao, M.N.; Bulliard, M. (Genaera Corp.); Stereoselective synthesis of 24-hydroxylated cpds. useful for the preparation of aminosterols, vitamin D analogs, and other cpds.. WO 9824800 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(CXIX)	53797	(5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl benzoate	n/a	C₃₄H₅₀O₄	详情	详情
(CXX)	53798	(5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-1,5-dimethyl-4-(sulfooxy)hexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl benzoate	n/a	C₃₄H₅₀O₇S	详情	详情
(CXXI)	53799	(1R,4R)-4-[(5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-isopropylpentyl hydrogen sulfate	n/a	C₂₇H₄₆O₆S	详情	详情
(CXXII)	53800	4-[(3-aminopropyl)amino]butanenitrile	n/a	C₇H₁₅N₃	详情	详情
(CXXIII)	53801	(1R,4R)-4-[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-({3-[(3-cyanopropyl)amino]propyl}amino)-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-isopropylpentyl hydrogen sulfate	n/a	C₃₄H₆₁N₃O₅S	详情	详情

Extended Information