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【结 构 式】

【分子编号】53714

【品名】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

【CA登记号】n/a

【 分 子 式 】C35H62O3Si

【 分 子 量 】558.96098

【元素组成】C 75.21% H 11.18% O 8.59% Si 5.02%

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:(XXX)

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.

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