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【结 构 式】

【分子编号】57898

【品名】(1R)-1-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-nitro-1-ethanol

【CA登记号】

【 分 子 式 】C14H23NO4Si

【 分 子 量 】297.42646

【元素组成】C 56.54% H 7.79% N 4.71% O 21.52% Si 9.44%

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:(IV)

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
Extended Information