(2R,3R)-methyl 3-hydroxy-2-iodo-3-phenylpropanoate | 757232-71-6

• 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: (2R,3R)-methyl 3-hydroxy-2-iodo-3-phenylpropanoate
• 英文别名: (-)-methyl (2R,3R)-3-hydroxy-2-iodo-3-phenylpropanoate；methyl (2R,3R)-3-hydroxy-2-iodo-3-phenylpropanoate
• CAS: 757232-71-6
• 化学式: C₁₀H₁₁IO₃
• 分子量: 306.1
• InChiKey: FSEFURWCHKSGHN-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-methyl 3-hydroxy-2-iodo-3-phenylpropanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 生成 methyl trans-3-phenylglycidate
  参考文献：
  名称：

  Chemoenzymatic approach to optically active phenylglycidates: resolution of bromo- and iodohydrins

  摘要：

  Enantiomerically enriched phenylglycidates, precursors of the taxol C-13 phenylisoserine side chain and diltiazem. were prepared by kinetic resolution of anti-2-bromo-3-hydroxy- and anti-3-hydroxy-2-iodophenylpropanoates to provide enantioriched (2R,3R)- and (2S,3S)-halohydrins. The bulkiness and inflexibility of bromo and iodo groups in halohydrins have made them inaccessible to the active site of most of the lipases utilized for the hydrolysis of their acyloxy derivatives. In a set of 22 hydrolases screened herein, including native as well as commercial enzymes, only Aspergillus niger (Lipase AS, AMANO) could catalyze the hydrolysis with high enantioselectivity (E = 176). The resolved halohydrins easily underwent transformation to the corresponding (2S,3R)- and (2R,3S)phenylglycidates. (C) 26 E'lsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.026
• 作为产物：
  描述：

  Methyl cinnamate 在 4-二甲氨基吡啶 、 phosphate buffer 、 lipase AS Amano 、 sodium hydrogensulfite 、 过碘酸 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 68.0h， 生成 (2R,3R)-methyl 3-hydroxy-2-iodo-3-phenylpropanoate
  参考文献：
  名称：

  Chemoenzymatic approach to optically active phenylglycidates: resolution of bromo- and iodohydrins

  摘要：

  Enantiomerically enriched phenylglycidates, precursors of the taxol C-13 phenylisoserine side chain and diltiazem. were prepared by kinetic resolution of anti-2-bromo-3-hydroxy- and anti-3-hydroxy-2-iodophenylpropanoates to provide enantioriched (2R,3R)- and (2S,3S)-halohydrins. The bulkiness and inflexibility of bromo and iodo groups in halohydrins have made them inaccessible to the active site of most of the lipases utilized for the hydrolysis of their acyloxy derivatives. In a set of 22 hydrolases screened herein, including native as well as commercial enzymes, only Aspergillus niger (Lipase AS, AMANO) could catalyze the hydrolysis with high enantioselectivity (E = 176). The resolved halohydrins easily underwent transformation to the corresponding (2S,3R)- and (2R,3S)phenylglycidates. (C) 26 E'lsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.026

文献信息

• Stereoselective chemoenzymatic process for the preparation of optically enriched phenylglycidates as precursors of taxol side chain
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL

  公开号：US20040259943A1

  公开（公告）日：2004-12-23

  The present invention relates to a novel and efficient chemoenzymatic process of preparation of optically active trans alkyl phenylglycidates. The invention particularly discloses a novel process for the chemoenzymatic synthesis of two enantiomers of trans alkyl phenylglycidate i.e. alkyl(2S,3R)-phenylglycidate and alkyl(2R,3S)-phenylglycidate of formulae 7 and 8 respectively. 1

  本发明涉及一种新颖有效的化学酶法制备光学活性反式烷基苯基乙二酸酯的方法。该发明特别揭示了一种新的化学酶法合成反式烷基苯基乙二酸酯的两个对映异构体，即式7和式8的烷基(2S,3R)-苯基乙二酸酯和烷基(2R,3S)-苯基乙二酸酯。
• US7060471B2
  申请人：——

  公开号：US7060471B2

  公开（公告）日：2006-06-13