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【结 构 式】

【分子编号】53759

【品名】1-(2-bromoethyl)-2-methylpropyl tert-butyl(dimethyl)silyl ether; [1-(2-bromoethyl)-2-methylpropoxy](tert-butyl)dimethylsilane

【CA登记号】n/a

【 分 子 式 】C12H27BrOSi

【 分 子 量 】295.33528

【元素组成】C 48.8% H 9.21% Br 27.06% O 5.42% Si 9.51%

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:(LXXIX)

In another synthetic route from pregnenolone acetate (LXXIII), its ketalization to (LXXIV) followed by allylic oxidation led to enone (LXXV). Sequential reduction of (LXXV) with lithium in liquid ammonia and then with K-Selectride gave alcohol (LXXVI), which was further protected as the methoxymethyl derivative (LXXVII). Selective deprotection of the C-20 ketal of (LXXVII) yielded ketone (LXXVIII). Ylide (LXXX) was prepared by condensation of bromide (LXXIX) with triphenylphosphine, followed by deprotonation with n-BuLi. Wittig condensation of ketone (LXXVIII) with phosphorane (LXXX) furnished olefin (LXXXI). Then, double-bond hydrogenation and deprotection of the 7-hydroxyl group of (LXXXI) gave rise to the intermediate (XI).

1 Moriarty, R.M.; Guo, L.; Tuladhar, S.M. (Genaera Corp.); Chemical synthesis of squalamine. WO 9419366 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 53697 (3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate n/a C35H64O4Si 详情 详情
(LXXIII) 35173 (3S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 1778-02-5 C23H34O3 详情 详情
(LXXIV) 53754 (3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate n/a C25H38O4 详情 详情
(LXXV) 53755 (3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate n/a C25H36O5 详情 详情
(LXXVI) 53756 (3S,5S,7R,8R,9S,10S,13S,14S,17S)-7-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate n/a C25H40O5 详情 详情
(LXXVII) 53757 (3S,5S,7R,8R,9S,10S,13S,14S,17S)-7-(methoxymethoxy)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate n/a C27H44O6 详情 详情
(LXXVIII) 53758 (3S,5S,7R,8R,9S,10S,13S,14S,17S)-17-acetyl-7-(methoxymethoxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate n/a C25H40O5 详情 详情
(LXXIX) 53759 1-(2-bromoethyl)-2-methylpropyl tert-butyl(dimethyl)silyl ether; [1-(2-bromoethyl)-2-methylpropoxy](tert-butyl)dimethylsilane n/a C12H27BrOSi 详情 详情
(LXXX) 53760 (3-{[tert-butyl(dimethyl)silyl]oxy}-4-methylpentylidene)(triphenyl)phosphorane; tert-butyl(dimethyl)silyl 2-methyl-1-[2-(triphenylphosphoranylidene)ethyl]propyl ether n/a C30H41OPSi 详情 详情
(LXXXI) 53761 (3S,5S,7R,8R,9S,10S,13S,14S,17R)-17-((Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethyl-1-hexenyl)-7-(methoxymethoxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate n/a C37H66O5Si 详情 详情
Extended Information