C-[(R)-C-[(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-oxiranyl]-C-(2-methoxymethoxymethyl-phenyl)]-methylamine | 143290-34-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: C-[(R)-C-[(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-oxiranyl]-C-(2-methoxymethoxymethyl-phenyl)]-methylamine
• 英文别名: (R)-[(2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]-[2-(methoxymethoxymethyl)phenyl]methanamine
• CAS: 143290-34-0
• 化学式: C₁₉H₃₃NO₄Si
• 分子量: 367.561
• InChiKey: JOVSWKHFXMULSR-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S,3S)-3-cyano-2,3-epoxy-1-propanol TBS ether 、 在 sodium tetrahydroborate 、 三甲基氯硅烷 作用下， 生成 C-[(R)-C-[(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-oxiranyl]-C-(2-methoxymethoxymethyl-phenyl)]-methylamine 、 C-[(S)-C-[(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-oxiranyl]-C-(2-methoxymethoxymethyl-phenyl)]-methylamine
  参考文献：
  名称：

  Chiral .alpha.,.beta.-epoxy group as a stereocontrolling element in the reduction of N-metalloimines. A short synthesis of anti-epoxy amines

  摘要：

  Reduction of the alpha,beta-epoxy N-metalloimines generated from the TBS ether of (2S,3S)-3-cyano-2,3-epoxy-1-propanol (1), Grignard reagents, and Me3SiCl with NaBH4 afforded the TBS ethers of (2S,3S,4S)-4-amino-2,3-epoxy-1-alkanols 4 with diastereoselectivities of up to 95:5.

  DOI：

  10.1021/jo00045a006

文献信息

• Chiral .alpha.,.beta.-epoxy group as a stereocontrolling element in the reduction of N-metalloimines. A short synthesis of anti-epoxy amines
  作者：Hirokazu Urabe、Yoshiaki Aoyama、Fumie Sato

  DOI：10.1021/jo00045a006

  日期：1992.9

  Reduction of the alpha,beta-epoxy N-metalloimines generated from the TBS ether of (2S,3S)-3-cyano-2,3-epoxy-1-propanol (1), Grignard reagents, and Me3SiCl with NaBH4 afforded the TBS ethers of (2S,3S,4S)-4-amino-2,3-epoxy-1-alkanols 4 with diastereoselectivities of up to 95:5.