methyl (2R,3S)-2,3-dihydroxy-3-(4'-chlorophenyl)propanoate | 206346-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2R,3S)-2,3-dihydroxy-3-(4'-chlorophenyl)propanoate
• 英文别名: methyl (2R,3S)-2,3-dihydroxy-3-(p-chlorophenyl)propionate；methyl (2R,3S)-3-(4-chlorophenyl)-2,3-dihydroxypropanoate
• CAS: 206346-40-9
• 化学式: C₁₀H₁₁ClO₄
• 分子量: 230.648
• InChiKey: QXKCOXIAKQIEGN-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-2,3-dihydroxy-3-(4'-chlorophenyl)propanoate 在 palladium on activated charcoal sodium azide 、 氢溴酸 、 氢气 、 sodium acetate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  脂肪酶催化的酯交换反应是制备高手性顺-1，2-二醇的可行途径。紫杉醇侧链的合成

  摘要：

  syn -2,3-二羟基-3-苯基丙酸甲酯（1a）及其简单衍生物（1b-e）在LPS催化的酯交换反应中得到有效拆分，从而导致紫杉醇侧链及其类似物的合成拆分的对映体。

  DOI：

  10.1016/s0040-4039(98)00147-6
• 作为产物：
  描述：

  对氯肉桂酸 在 四氧化锇 、 N-甲基吲哚酮 、 硫酸 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 methyl (2R,3S)-2,3-dihydroxy-3-(4'-chlorophenyl)propanoate
  参考文献：
  名称：

  The asymmetric synthesis of β-aryl-α-hydroxy esters from β-aryl-α,β-dihydroxy esters

  摘要：

  alpha,beta-Dihydroxy-beta-aryl esters obtained via Sharpless asymmetric dihydroxylation (AD) of substituted cinnamate esters are reduced by sequential reaction with trimethyl orthoacetate and acetyl bromide followed by catalytic hydrogenolysis in methanol to give enantiomerically enriched beta-aryl-alpha-hydroxy esters. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01176-0

文献信息

• Aldol Reactions with Erythrulose Derivatives: Stereoselective Synthesis of Differentially Protected syn -α,β-Dihydroxy Esters
  作者：M. Carda、J. Murga、E. Falomir、F. González、J.A. Marco

  DOI：10.1016/s0040-4020(99)01041-8

  日期：2000.1

  Boron enolates of 1-O-silylated erythrulose 3,4-acetonides prepared with Brown's chloro-dicyclohexylborane/tertiary amine system have been shown to react with achiral aldehydes in a highly stereoselective way to yield a 1,2-syn/1,3-syn stereoisomer. Through oxidative cleavage of the aldol adducts with periodic acid hydrate, enantiopure syn-alpha,beta-dihydroxy esters with either hydroxyl group differently protected have been prepared. These erythrulose derivatives therefore behave as a chiral hydroxy acetate (glycolate) enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Lipase-catalyzed transesterification as a practical route to homochiral syn-1,2-diols. The synthesis of the taxol side chain
  作者：Donghyun Lee、Mahn-Joo Kim

  DOI：10.1016/s0040-4039(98)00147-6

  日期：1998.4

  syn-2,3-Dihydoxy-3-phenyl-propanoic acid methyl ester (1a) and its simple derivatives (1b-e) are efficiently resolved in LPS-catalyzed transesterification, leading to the synthesis of the taxol side chain and analogs from both resolved enantiomers.

  syn -2,3-二羟基-3-苯基丙酸甲酯（1a）及其简单衍生物（1b-e）在LPS催化的酯交换反应中得到有效拆分，从而导致紫杉醇侧链及其类似物的合成拆分的对映体。
• The asymmetric synthesis of β-aryl-α-hydroxy esters from β-aryl-α,β-dihydroxy esters
  作者：Nicholas J Lawrence、Stephen Brown

  DOI：10.1016/s0040-4020(01)01176-0

  日期：2002.1

  alpha,beta-Dihydroxy-beta-aryl esters obtained via Sharpless asymmetric dihydroxylation (AD) of substituted cinnamate esters are reduced by sequential reaction with trimethyl orthoacetate and acetyl bromide followed by catalytic hydrogenolysis in methanol to give enantiomerically enriched beta-aryl-alpha-hydroxy esters. (C) 2002 Elsevier Science Ltd. All rights reserved.