(2R,3S)-3-amino-4-phenylbutane-1,2-diol | 109389-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-3-amino-4-phenylbutane-1,2-diol
• CAS: 109389-10-8
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: YXQDBEZPBMCYAI-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.09
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.48
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-amino-4-phenylbutane-1,2-diol 在 吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Acetic acid (1R,2S)-1-bromomethyl-2-tert-butoxycarbonylamino-3-phenyl-propyl ester
  参考文献：
  名称：

  An efficient synthesis of N-protected threo (2R,3S)-3-amino-1,2-epoxy phenylbutane

  摘要：

  A precise and versatile method was developed for the synthesis of threo amino epoxide derivatives, which are useful intermediates for protease inhibitors. it involves the diastereoselective reduction of the carbonyl group of gamma-N,N-dibenzyl amino a-hydroxy beta-keto sulfide prepared from an amino acid, and its subsequent stereospecific conversion to an amino epoxide via acetoxy halogenation in high yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.134
• 作为产物：
  描述：

  (3S)-3-(N,N-dibenzyl)amino-1-hydroxy-1-methylthio-2-oxo-4-phenylbutane 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.83h， 生成 (2R,3S)-3-amino-4-phenylbutane-1,2-diol
  参考文献：
  名称：

  An efficient synthesis of N-protected threo (2R,3S)-3-amino-1,2-epoxy phenylbutane

  摘要：

  A precise and versatile method was developed for the synthesis of threo amino epoxide derivatives, which are useful intermediates for protease inhibitors. it involves the diastereoselective reduction of the carbonyl group of gamma-N,N-dibenzyl amino a-hydroxy beta-keto sulfide prepared from an amino acid, and its subsequent stereospecific conversion to an amino epoxide via acetoxy halogenation in high yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.134

文献信息

• An efficient synthesis of N-protected threo (2R,3S)-3-amino-1,2-epoxy phenylbutane
  作者：Takayuki Suzuki、Yutaka Honda、Kunisuke Izawa

  DOI：10.1016/j.tetlet.2005.06.134

  日期：2005.8

  A precise and versatile method was developed for the synthesis of threo amino epoxide derivatives, which are useful intermediates for protease inhibitors. it involves the diastereoselective reduction of the carbonyl group of gamma-N,N-dibenzyl amino a-hydroxy beta-keto sulfide prepared from an amino acid, and its subsequent stereospecific conversion to an amino epoxide via acetoxy halogenation in high yield. (c) 2005 Elsevier Ltd. All rights reserved.