(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-chloroacetoxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine | 316139-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-chloroacetoxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine
• 英文别名: tert-butyl (2R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[4-[(1S)-1-(2-chloroacetyl)oxy-3-ethoxy-3-oxopropyl]phenyl]pyrrolidine-1-carboxylate
• CAS: 316139-44-3
• 化学式: C₂₈H₄₄ClNO₇Si
• 分子量: 570.198
• InChiKey: ANYRVQCCBWGMKE-ZLNRFVROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-chloroacetoxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以92%的产率得到(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of ethyl 3-aryl-3-hydroxypropionate: preparation of the side chain of a novel carbapenem, J-114,870

  摘要：

  An optically active 3-aryl-3-hydroxypropionate 3a was prepared by lipase-catalyzed kinetic hydrolysis of a diastereomeric mixture of 3-aryl-3-(alpha -chloroacetoxy)propionate 6 in good conversion yield with adequate purity (>95% de). This enzymatic reaction proceeded with great efficiency as measured by reaction rate, chemical yield and stereoselectivity. The compound 3a was converted to J-114,870 1a, a novel ultra-broad spectrum carbapenem without significant epimerization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00326-8
• 作为产物：
  描述：

  (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-(1-chloroacetoxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine 在 lipase 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以44%的产率得到(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((R)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of ethyl 3-aryl-3-hydroxypropionate: preparation of the side chain of a novel carbapenem, J-114,870

  摘要：

  An optically active 3-aryl-3-hydroxypropionate 3a was prepared by lipase-catalyzed kinetic hydrolysis of a diastereomeric mixture of 3-aryl-3-(alpha -chloroacetoxy)propionate 6 in good conversion yield with adequate purity (>95% de). This enzymatic reaction proceeded with great efficiency as measured by reaction rate, chemical yield and stereoselectivity. The compound 3a was converted to J-114,870 1a, a novel ultra-broad spectrum carbapenem without significant epimerization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00326-8

文献信息

• Lipase-catalyzed kinetic resolution of ethyl 3-aryl-3-hydroxypropionate: preparation of the side chain of a novel carbapenem, J-114,870
  作者：Yuichi Sugimoto、Hideaki Imamura、Aya Shimizu、Masato Nakano、Shigeru Nakajima、Shinnosuke Abe、Koji Yamada、Hajime Morishima

  DOI：10.1016/s0957-4166(00)00326-8

  日期：2000.9

  An optically active 3-aryl-3-hydroxypropionate 3a was prepared by lipase-catalyzed kinetic hydrolysis of a diastereomeric mixture of 3-aryl-3-(alpha -chloroacetoxy)propionate 6 in good conversion yield with adequate purity (>95% de). This enzymatic reaction proceeded with great efficiency as measured by reaction rate, chemical yield and stereoselectivity. The compound 3a was converted to J-114,870 1a, a novel ultra-broad spectrum carbapenem without significant epimerization. (C) 2000 Elsevier Science Ltd. All rights reserved.