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【结 构 式】

【分子编号】42453

【品名】(4R)-4-[(1S)-2-[[tert-butyl(diphenyl)silyl]oxy]-1-[(triethylsilyl)oxy]ethyl]-4-hydroxy-N-methoxy-N-methyloctanamide

【CA登记号】

【 分 子 式 】C34H57NO5Si2

【 分 子 量 】616.00132

【元素组成】C 66.29% H 9.33% N 2.27% O 12.99% Si 9.12%

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:(VI)

Synthesis of Weinreb amide (VII). The reaction of the chiral epoxide (I) with HOAc in THF, followed by cyclization with TsOH in methanol gives the chiral tetrahydrofuran derivative (II), which is selectively monosilylated with TBDPSCl and imidazole, yielding silyl ether (III). The silylation of (III) with Tes-Cl affords the disilylated compound (IV), which is oxidized with RuCl3 and NaIO4 in acetonitrile/CCl4/pH 8 buffer to provide the lactone (V). The reaction of (V) with N,O-dimethylhydroxylamine and Me2AlCl in dichloromethane gives the amide (VI), which is finally protected to afford the desired target intermediate (VII).

1 Shimizu, T.; et al.; Total synthesis of reveromycin A. Org Lett 2000, 2, 14, 2153.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 42448 [(2R,3R)-3-butyl-3-[4-(tetrahydro-2H-pyran-2-yloxy)butyl]oxiranyl]methanol C16H30O4 详情 详情
(II) 42449 (1S)-1-[(2R)-2-butyltetrahydro-2-furanyl]-1,2-ethanediol C10H20O3 详情 详情
(III) 42450 (1S)-2-[[tert-butyl(diphenyl)silyl]oxy]-1-[(2R)-2-butyltetrahydro-2-furanyl]-1-ethanol C26H38O3Si 详情 详情
(IV) 42451 (6S)-6-[(2R)-2-butyltetrahydro-2-furanyl]-8,8-diethyl-2,2-dimethyl-3,3-diphenyl-4,7-dioxa-3,8-disiladecane; tert-butyl(diphenyl)silyl (2S)-2-[(2R)-2-butyltetrahydro-2-furanyl]-2-[(triethylsilyl)oxy]ethyl ether C32H52O3Si2 详情 详情
(V) 42452 (5R)-5-butyl-5-[(1S)-2-[[tert-butyl(diphenyl)silyl]oxy]-1-[(triethylsilyl)oxy]ethyl]dihydro-2(3H)-furanone C32H50O4Si2 详情 详情
(VI) 42453 (4R)-4-[(1S)-2-[[tert-butyl(diphenyl)silyl]oxy]-1-[(triethylsilyl)oxy]ethyl]-4-hydroxy-N-methoxy-N-methyloctanamide C34H57NO5Si2 详情 详情
(VII) 42454   C35H59NO5Si2 详情 详情
Extended Information