【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% |
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 |