(2R,3S)-3-methyl-4-oxo-4-phenyl-2-{[(1R)-1-phenylethyl]amino}butanoic acid | 1220353-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-3-methyl-4-oxo-4-phenyl-2-{[(1R)-1-phenylethyl]amino}butanoic acid
• 英文别名: (2R,3S)-3-methyl-4-oxo-4-phenyl-2-[[(1R)-1-phenylethyl]amino]butanoic acid
• CAS: 1220353-58-1
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: IEHXKQNLEXUVTN-JJRVBVJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-methyl-4-oxo-4-phenyl-2-{[(1R)-1-phenylethyl]amino}butanoic acid 在 盐酸 、 sodium tetrahydroborate 、 20 wt% Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 20.0~80.0 ℃ 、110.0 kPa 条件下， 反应 4.25h， 生成 (1R,2S,3R)-3-amino-2-methyl-1-phenylbutane-1,4-diol acetate
  参考文献：
  名称：

  Expedient and Practical Synthesis of CERT-Dependent Ceramide Trafficking Inhibitor HPA-12 and Its Analogues

  摘要：

  The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-dependent ceramide trafficking HPA-12 from (R,R)-anti- to the (R,S)-syn-enantiomer. Due to the expeditiousness of production and inexpensive conditions developed, a series of alkyl- and aryl-substituted analogues of HPA-12 is also reported.

  DOI：

  10.1021/ol2001057
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 苯丙酮 、 乙醛酸 以 乙醇 为溶剂， 反应 144.0h， 以48%的产率得到(2R,3S)-3-methyl-4-oxo-4-phenyl-2-{[(1R)-1-phenylethyl]amino}butanoic acid
  参考文献：
  名称：

  The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction

  摘要：

  The novel synthesis of highly enantioenriched N-substituted alpha-amino-gamma-alkyl(aryl)-gamma-oxoutanoic acids is described The process involves the combination of a crystallization-induced asymmetric transformation (CIAT) and the Mannich reaction The role of retro-Mannich and retro-Michael reactions in the mechanism of the highly stereoselective transformation is also discussed. (c) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2009.12.014

文献信息

• Expedient and Practical Synthesis of CERT-Dependent Ceramide Trafficking Inhibitor HPA-12 and Its Analogues
  作者：Andrej Ďuriš、Tomáš Wiesenganger、Daniela Moravčíková、Peter Baran、Jozef Kožíšek、Adam Daïch、Dušan Berkeš

  DOI：10.1021/ol2001057

  日期：2011.4.1

  The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-dependent ceramide trafficking HPA-12 from (R,R)-anti- to the (R,S)-syn-enantiomer. Due to the expeditiousness of production and inexpensive conditions developed, a series of alkyl- and aryl-substituted analogues of HPA-12 is also reported.
• The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction
  作者：Pavol Jakubec、Pavel Petráš、Andrej Ďuriš、Dušan Berkeš

  DOI：10.1016/j.tetasy.2009.12.014

  日期：2010.1

  The novel synthesis of highly enantioenriched N-substituted alpha-amino-gamma-alkyl(aryl)-gamma-oxoutanoic acids is described The process involves the combination of a crystallization-induced asymmetric transformation (CIAT) and the Mannich reaction The role of retro-Mannich and retro-Michael reactions in the mechanism of the highly stereoselective transformation is also discussed. (c) 2009 Elsevier Ltd All rights reserved