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【结 构 式】 
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【分子编号】57899 【品名】(1R)-2-amino-1-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-ethanol 【CA登记号】 |
【 分 子 式 】C14H25NO2Si 【 分 子 量 】267.44354 【元素组成】C 62.87% H 9.42% N 5.24% O 11.96% Si 10.5% |
合成路线1
该中间体在本合成路线中的序号：(V)The enantioselective condensation of 4-(tert-butyldimethylsilyloxy)benzaldehyde (I) with nitromethane (II), catalyzed by the chiral Zn ligand complex (III) in THF gives the (R)-2-nitroethanol derivative (IV), which is reduced with H2 over Pd/C in ethanol to yield the 2-aminoethanol derivative (V). The condensation of (V) with carboxylic acid (VI) by means of 2,2-dimethylpropanoyl chloride and DIEA in THF affords the corresponding amide (VII), which is reduced with LiAlH4 in Et2O to yield the protected hydroxyamine (VIII). Finally, this compound is desilylated by means of HCl and KF in MeOH to furnish the target tetrahydroxyamine derivative.
| 【1】 Ito, H.; Bremeyer, N.; Trost, B.M.; Yeh, V.S.C.; Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine. Org Lett 2002, 4, 16, 2621. |
| 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) | 57897 | 4-{[tert-butyl(dimethyl)silyl]oxy}benzaldehyde | C13H20O2Si | 详情 | 详情 | |
| (II) | 39563 | nitromethane | 75-52-5 | CH3NO2 | 详情 | 详情 |
| (III) | 57893 | C64H60O3Zn2 | 详情 | 详情 | ||
| (IV) | 57898 | (1R)-1-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-nitro-1-ethanol | C14H23NO4Si | 详情 | 详情 | |
| (V) | 57899 | (1R)-2-amino-1-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-ethanol | C14H25NO2Si | 详情 | 详情 | |
| (VI) | 24049 | 2-(3,4-dimethoxyphenyl)acetic acid | 93-40-3 | C10H12O4 | 详情 | 详情 |
| (VII) | 57900 | N-[(2R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-hydroxyethyl]-2-(3,4-dimethoxyphenyl)acetamide | C24H35NO5Si | 详情 | 详情 | |
| (VIII) | 57901 | (1R)-1-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanol | C24H37NO4Si | 详情 | 详情 |