(3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol -Drug Synthesis Database

【结构式】

【分子编号】53722

【品名】(3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol

【CA登记号】n/a

【分子式】C₄₀H₆₈O₃Si

【分子量】625.06362

【元素组成】C 76.86% H 10.97% O 7.68% Si 4.49%

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：(XXXVIII)

After silylation of alcohol (XXXVI) to silyl ether (XXXVII), its tetrahydropyranyl protecting group was selectively removed by treatment with magnesium bromide in Et2O. The resultant 3-beta alcohol (XXXVIII) was oxidized to ketone (XXXIX) employing Collin's reagent. The polyamino side-chain was then introduced in (XXXIX) by reductive amination with the di-Boc-protected spermidine (XL) in the presence of NaBH3CN, giving (XLI) as a mixture of 3-alpha and 3-beta isomers.

参考文献中间体

合成目标

【1】 Pechulis, A.D.; et al.; Synthesis of 24xi-squalamine, an anti-infective steroidal polyamine. J Org Chem 1995, 60, 16, 5121.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXXVI)	53720	(6R)-6-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-3-heptanol	n/a	C₃₉H₆₂O₄	详情	详情
(XXXVII)	53721	({(4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-isopropylpentyl}oxy)(tert-butyl)dimethylsilane; benzyl (3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl ether	n/a	C₄₅H₇₆O₄Si	详情	详情
(XXXVIII)	53722	(3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol	n/a	C₄₀H₆₈O₃Si	详情	详情
(XXXIX)	53723	(5S,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one	n/a	C₄₀H₆₆O₃Si	详情	详情
(XL)	53724	tert-butyl 3-aminopropyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate	n/a	C₁₇H₃₅N₃O₄	详情	详情
(XLI)	53725	tert-butyl 3-{[(5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino}propyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate	n/a	C₅₇H₁₀₁N₃O₆Si	详情	详情

Extended Information