Ethyl (2S,3R)-3-chloro-2-hydroxy-4-phenylbutanoate | 145475-56-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl (2S,3R)-3-chloro-2-hydroxy-4-phenylbutanoate
• CAS: 145475-56-5
• 化学式: C₁₂H₁₅ClO₃
• 分子量: 242.702
• InChiKey: PBKSJBDRYWZQAU-GHMZBOCLSA-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 (2S,3R)-3-chloro-2-hydroxy-4-phenylbutanoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以76.5%的产率得到(R)-2-羟基-4-苯基丁酸乙酯
  参考文献：
  名称：

  Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters

  摘要：

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.

  DOI：

  10.1021/jo00054a036
• 作为产物：
  描述：

  2-氧代-4-苯基丁酸乙酯 在 lithium chloride 、 copper dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 Ethyl (2S,3R)-3-chloro-2-hydroxy-4-phenylbutanoate
  参考文献：
  名称：

  Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters

  摘要：

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.

  DOI：

  10.1021/jo00054a036

文献信息

• A highly enantioselective chemoenzymatic synthesis of syn-3-amino-2-hydroxy esters: key intermediates for taxol side chain and phenylnorstatine
  作者：J. Augusto R. Rodrigues、Humberto M.S. Milagre、Cíntia D.F. Milagre、Paulo J.S. Moran

  DOI：10.1016/j.tetasy.2005.08.015

  日期：2005.9

  Starting from the bromination of α-ketoesters to obtain 3-bromo-2-oxoalkanoates and bioreduction with Saccharomyces cerevisiae entrapped in calcium alginate pellets with double gel layers, syn-(2R,3S)-β-bromo-α-hydroxy esters were obtained regioselectively in high yields and high ee. These chiral bromohydrins were cyclized to epoxides that were transformed into oxazolidines and finally opened by acidic

  从α-酮酸酯的溴化反应开始，获得3-溴-2-氧代链烷酸酯，并用包埋在具有双层凝胶层的藻酸钙沉淀中的酿酒酵母进行生物还原，合成了顺式-（2 R，3 S）-β-溴-α-羟基酯以高产率和高ee区域选择性地获得。这些手性溴醇被环化成环氧化物，然后被转化为恶唑烷，最后通过酸性水解打开，从而以高总收率和高ee产率得到合成-（2 S，3 S）-β-氨基-α-羟基酯。在反应过程中，所有中间体的对映体过量均得以维持。
• Asymmetric Bioreduction of Ethyl 3-Halo-2-oxo-4-phenylbutanoate by <i>Saccharomyces </i><i>c</i><i>erevisiae</i> Immobilized in Ca-Alginate Beads with Double Gel Layer
  作者：Humberto M. S. Milagre、Cíntia D. F. Milagre、Paulo J. S. Moran、Maria Helena A. Santana、J. Augusto R. Rodrigues

  DOI：10.1021/op0502497

  日期：2006.5.1

  The asymmetric bioreduction of ethyl 3-halo-2-oxo-4- phenylbutanoate was studied for several microorganisms and especially for Saccharomyces cerevisiae. The highest chemical yield (90%), de (70%) and ee (96-99%) were obtained with S. cerevisiae immobilized in calcium alginate beads with double gel layers, and reaction conditions were optimized by changing matrix of immobilization, concentration of substrate, and feeding with glucose as electron donor. The entrapment of cells with double gel layers was fundamental to achieve high enantio- and diastereoselectivity.