ethyl (2R,3S)-2-chloro-3-hydroxy-4-phenylbutyrate | 832110-38-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl (2R,3S)-2-chloro-3-hydroxy-4-phenylbutyrate
• 英文别名: ethyl (2R,3S)-2-chloro-3-hydroxy-4-phenylbutanoate
• CAS: 832110-38-0
• 化学式: C₁₂H₁₅ClO₃
• 分子量: 242.702
• InChiKey: UCFCLRSWVRCMHX-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2R,3S)-2-chloro-3-hydroxy-4-phenylbutyrate 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以99%的产率得到ethyl (2S,3S)-3-benzyloxirane-2-carboxylate
  参考文献：
  名称：

  Chemoenzymatic formal total synthesis of (−)-bestatin

  摘要：

  A highly stereoselective, enzymatic reduction of an alpha-chloro-beta-keto ester provided the key intermediate for a total synthesis of the alpha-hydroxy-beta-amino acid moiety of (-)-bestatin. The reduction product was cyclized to a glycidic ester that was opened in a Ritter reaction with benzonitrile, affording a trans-oxazoline, which was hydrolyzed under acidic conditions to the target molecule. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.022
• 作为产物：
  描述：

  4-苯基乙酰乙酸乙酯 在 KPi buffer 、 XAD-4 resin 磺酰氯 、 air 、 葡萄糖 、 Escherichia coli BL₂₁(DE₃)(pIK₄) overexpressing reductase 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 ethyl (2R,3S)-2-chloro-3-hydroxy-4-phenylbutyrate
  参考文献：
  名称：

  Chemoenzymatic formal total synthesis of (−)-bestatin

  摘要：

  A highly stereoselective, enzymatic reduction of an alpha-chloro-beta-keto ester provided the key intermediate for a total synthesis of the alpha-hydroxy-beta-amino acid moiety of (-)-bestatin. The reduction product was cyclized to a glycidic ester that was opened in a Ritter reaction with benzonitrile, affording a trans-oxazoline, which was hydrolyzed under acidic conditions to the target molecule. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.022

文献信息

• Stereoselective, Biocatalytic Reductions of α-Chloro-β-keto Esters
  作者：Iwona A. Kaluzna、Brent D. Feske、Weerawut Wittayanan、Ion Ghiviriga、Jon D. Stewart

  DOI：10.1021/jo0484981

  日期：2005.1.1

  Eighteen known and putative reductases from baker's yeast (Saccharomyces cerevisiae) were tested for the ability to reduce a series of alpha-chloro-beta-keto esters. In nearly all cases, it was possible to produce at least two of the four possible alpha-chloro-beta-hydroxy ester diastereomers with high optical purities. The utility of this approach was demonstrated by reducing ethyl 2-chloroacetoacetate to the corresponding Syn-(2R,3S)-alcohol on a multigram scale using whole cells of an Escherichia coli strain overexpressing a single yeast reductase identified from the screening studies.
• Chemoenzymatic formal total synthesis of (−)-bestatin
  作者：Brent D. Feske、Jon D. Stewart

  DOI：10.1016/j.tetasy.2005.08.022

  日期：2005.9

  A highly stereoselective, enzymatic reduction of an alpha-chloro-beta-keto ester provided the key intermediate for a total synthesis of the alpha-hydroxy-beta-amino acid moiety of (-)-bestatin. The reduction product was cyclized to a glycidic ester that was opened in a Ritter reaction with benzonitrile, affording a trans-oxazoline, which was hydrolyzed under acidic conditions to the target molecule. (C) 2005 Elsevier Ltd. All rights reserved.