2-(4-(benzyloxy)benzyl)-3-ethoxy-2-methyl-3-oxopropanoic acid | 1187923-62-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-(4-(benzyloxy)benzyl)-3-ethoxy-2-methyl-3-oxopropanoic acid
• CAS: 1187923-62-1
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: ALONHPUODDLSJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4-(benzyloxy)benzyl)-3-ethoxy-2-methyl-3-oxopropanoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-(benzyloxy)benzyl)-3-ethoxy-2-methyl-3-oxopropanoic acid chloride
  参考文献：
  名称：

  Development of a practical mass spectrometry based assay for determining enantiomeric excess. A fast and convenient method for the optimization of PLE-catalyzed hydrolysis of prochiral disubstituted malonates

  摘要：

  A practical mass spectrometry-based enantioselectivity assay is presented which makes use of enantiomerically enriched, but not enantiomerically pure, probe molecules readily obtained from esterase hydrolysis of prochiral malonates. The technique presented here allows us to recycle materials obtained from esterase hydrolysis which give substantial. but synthetically insufficient, enantiomeric excess as probe molecules in an enantioselectivity assay. The enantiomerically enriched products are esterified using deuterium-labelled alcohol. The enantiomeric excess is measured using mass spectrometry (LC-MS and LDI) by measuring the D-5/H-5 ratio in the resulting products obtained from an enzymatic hydrolysis. The D-5/H-5 ratio is corrected to account for the enantiomeric purity of the probe. Herein we report the results obtained from Pig Liver Esterase hydrolyses of prochiral malonate esters and outline the strengths and limitations of this approach to enantioselectivity determinations. This assay strategy was able to identify reaction conditions that led to an improvement in ee from 70% ee to >97% ee in the PLE-catalyzed hydrolysis of a prochiral malonate used to prepare unnatural serine analogues. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.037
• 作为产物：
  描述：

  diethyl 2-(4-(benzyloxy)benzyl)-2-methylmalonate 在 sodium hydroxide 、 水 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以76%的产率得到2-(4-(benzyloxy)benzyl)-3-ethoxy-2-methyl-3-oxopropanoic acid
  参考文献：
  名称：

  Development of a practical mass spectrometry based assay for determining enantiomeric excess. A fast and convenient method for the optimization of PLE-catalyzed hydrolysis of prochiral disubstituted malonates

  摘要：

  A practical mass spectrometry-based enantioselectivity assay is presented which makes use of enantiomerically enriched, but not enantiomerically pure, probe molecules readily obtained from esterase hydrolysis of prochiral malonates. The technique presented here allows us to recycle materials obtained from esterase hydrolysis which give substantial. but synthetically insufficient, enantiomeric excess as probe molecules in an enantioselectivity assay. The enantiomerically enriched products are esterified using deuterium-labelled alcohol. The enantiomeric excess is measured using mass spectrometry (LC-MS and LDI) by measuring the D-5/H-5 ratio in the resulting products obtained from an enzymatic hydrolysis. The D-5/H-5 ratio is corrected to account for the enantiomeric purity of the probe. Herein we report the results obtained from Pig Liver Esterase hydrolyses of prochiral malonate esters and outline the strengths and limitations of this approach to enantioselectivity determinations. This assay strategy was able to identify reaction conditions that led to an improvement in ee from 70% ee to >97% ee in the PLE-catalyzed hydrolysis of a prochiral malonate used to prepare unnatural serine analogues. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.037

文献信息

• Development of a practical mass spectrometry based assay for determining enantiomeric excess. A fast and convenient method for the optimization of PLE-catalyzed hydrolysis of prochiral disubstituted malonates
  作者：Douglas S. Masterson、Dale A. Rosado、Cassie Nabors

  DOI：10.1016/j.tetasy.2009.05.037

  日期：2009.7

  A practical mass spectrometry-based enantioselectivity assay is presented which makes use of enantiomerically enriched, but not enantiomerically pure, probe molecules readily obtained from esterase hydrolysis of prochiral malonates. The technique presented here allows us to recycle materials obtained from esterase hydrolysis which give substantial. but synthetically insufficient, enantiomeric excess as probe molecules in an enantioselectivity assay. The enantiomerically enriched products are esterified using deuterium-labelled alcohol. The enantiomeric excess is measured using mass spectrometry (LC-MS and LDI) by measuring the D-5/H-5 ratio in the resulting products obtained from an enzymatic hydrolysis. The D-5/H-5 ratio is corrected to account for the enantiomeric purity of the probe. Herein we report the results obtained from Pig Liver Esterase hydrolyses of prochiral malonate esters and outline the strengths and limitations of this approach to enantioselectivity determinations. This assay strategy was able to identify reaction conditions that led to an improvement in ee from 70% ee to >97% ee in the PLE-catalyzed hydrolysis of a prochiral malonate used to prepare unnatural serine analogues. (C) 2009 Elsevier Ltd. All rights reserved.