(3S,8S,9S,10R,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-methylbutyl)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4,8,9,10,11,12,13,14,15,16,17-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one -Drug Synthesis Database

【结构式】

【分子编号】53715

【品名】(3S,8S,9S,10R,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-methylbutyl)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4,8,9,10,11,12,13,14,15,16,17-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one

【CA登记号】n/a

【分子式】C₃₅H₆₀O₄Si

【分子量】572.9445

【元素组成】C 73.37% H 10.56% O 11.17% Si 4.9%

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：(XXXI)

In a different method, protection of alcohol (III) as the tert-butyldimethylsilyl ether (XXX), followed by allylic oxidation by means of CrO3 in the presence of 3,5-dimethylpyrazole (DMP), gave enone (XXXI). Hydrogenation of (XXXI) using Adams catalyst resulted in the formation of the saturated ketone (XXXII). Some undesired 7-beta alcohol byproduct was reoxidized to ketone (XXXII) by means of Collin's reagent. Stereoselective reduction of ketone (XXXII) with K-Selectride afforded the 7-alpha alcohol (XXXIII), which was protected as the benzyl ether (XXXIV) by treatment with benzyl bromide and NaH. After desilylation of (XXXIV) with Bu4NF, the deprotected alcohol was subjected to Swern oxidation to provide aldehyde (XXXV). Addition of isopropylmagnesium chloride to aldehyde (XXXV) gave alcohol (XXXVI) as a mixture of epimers.

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
(III)	53689	(4R)-4-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-pentanol	n/a	C₂₉H₄₈O₃	详情	详情
(XXX)	53714	tert-butyl(dimethyl)silyl (4R)-4-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl ether; tert-butyl({(4R)-4-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl}oxy)dimethylsilane	n/a	C₃₅H₆₂O₃Si	详情	详情
(XXXI)	53715	(3S,8S,9S,10R,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-methylbutyl)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4,8,9,10,11,12,13,14,15,16,17-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one	n/a	C₃₅H₆₀O₄Si	详情	详情
(XXXII)	53716	(3S,5R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-methylbutyl)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-7H-cyclopenta[a]phenanthren-7-one	n/a	C₃₅H₆₂O₄Si	详情	详情
(XXXIII)	53717	(3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-methylbutyl)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-7-ol	n/a	C₃₅H₆₄O₄Si	详情	详情
(XXXIV)	53718	benzyl (3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-methylbutyl)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl ether; ({(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]pentyl}oxy)(tert-butyl)dimethylsilane	n/a	C₄₂H₇₀O₄Si	详情	详情
(XXXV)	53719	(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]pentanal	n/a	C₃₆H₅₄O₄	详情	详情
(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

Extended Information