ethyl (2S,3S)-2-chloro-3-hydroxybutanoate | 110444-42-3

• 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 (2S,3S)-2-chloro-3-hydroxybutanoate
• CAS: 110444-42-3
• 化学式: C₆H₁₁ClO₃
• 分子量: 166.605
• InChiKey: XWWGVYVLALKWDS-WHFBIAKZSA-N

物化性质

• 沸点：
  245.1±20.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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 (2S,3S)-2-chloro-3-hydroxybutanoate 、 caesium 4-chlorophenate 反应 120.0h， 以41%的产率得到ethyl (E)-2,3-epoxybutyrate
  参考文献：
  名称：

  Reaction of caesium 4-chlorophenate and chlorohydrins from threonines: synthesis of clofibrate analogues

  摘要：

  Clofibrate is a well-known peroxisome prolifierator-activated receptor-alpha (PPARalpha) agonist, used in the treatment of hyperlipaemias and atherosclerosis and to prevent heart failure. Herein, the preparation of the four enantiomerically pure stereoisomers of ethyl 2-(4-chlorophenoxy)-3-hydroxybutanoate as clofibrate analogues is described. Biological evaluation of these new compounds was performed by a transactivation assay in a transiently transfected monkey kidney fibroblast cell line. All four diastereomers were inactive even at 300 muM, where clofibrate showed an evident activity, suggesting that the designed clofibrate molecular structural modifications in the analogues caused the loss of peroxisome proliferator-activated receptor-alpha (PPARalpha) activity. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.006
• 作为产物：
  描述：

  2-氯乙酰乙酸乙酯 在 KP_i 、 YGL₁₅₇w GST-fusion protein from Saccharomyces cerevisiae D-葡萄糖-6-磷酸 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 glucose 6-phosphate dehydrogenase 作用下， 生成 ethyl 2-chloro-3-hydroxybutyrate 、 ethyl (2S,3S)-2-chloro-3-hydroxybutanoate
  参考文献：
  名称：

  Stereoselective, Biocatalytic Reductions of α-Chloro-β-keto Esters

  摘要：

  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.

  DOI：

  10.1021/jo0484981

文献信息

• The microbial reduction of 2-chloro-3-oxoesters
  作者：Odile Cabon、Didier Buisson、Marc Larcheveque、Robert Azerad

  DOI：10.1016/0957-4166(95)00294-y

  日期：1995.9

  Several aliphatic or aromatic 2-chloro-3-oxoesters are stereoselectively reduced by yeast or fungal strains, affording in fair to good yield and high enantiomeric excess some of the respective 2-chloro-3-hydroxyester stereoisomers.
• 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.
• Reaction of caesium 4-chlorophenate and chlorohydrins from threonines: synthesis of clofibrate analogues
  作者：Maria Grazia Perrone、Ernesto Santandrea、Leonardo Di Nunno、Antonio Scilimati、Vincenzo Tortorella、Francesco Capitelli、Valerio Bertolasi

  DOI：10.1016/j.tetasy.2005.01.006

  日期：2005.2

  Clofibrate is a well-known peroxisome prolifierator-activated receptor-alpha (PPARalpha) agonist, used in the treatment of hyperlipaemias and atherosclerosis and to prevent heart failure. Herein, the preparation of the four enantiomerically pure stereoisomers of ethyl 2-(4-chlorophenoxy)-3-hydroxybutanoate as clofibrate analogues is described. Biological evaluation of these new compounds was performed by a transactivation assay in a transiently transfected monkey kidney fibroblast cell line. All four diastereomers were inactive even at 300 muM, where clofibrate showed an evident activity, suggesting that the designed clofibrate molecular structural modifications in the analogues caused the loss of peroxisome proliferator-activated receptor-alpha (PPARalpha) activity. (C) 2005 Elsevier Ltd. All rights reserved.