(2S)-1,2-pyrrolidinecarboxylic acid 1-(2-(trimethylsilyl)ethyl) 2-methyl diester | 132592-25-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-1,2-pyrrolidinecarboxylic acid 1-(2-(trimethylsilyl)ethyl) 2-methyl diester
• 英文别名: (2S)-1-([2-trimethylsilyl]ethoxycarbonyl)-2-(methoxycarbonyl)pyrrolidine；(2S)-1,2-pyrrolidinecarboxylic acid 1-[2-(trimethylsilyl)ethyl] 2-methyl diester；2-O-methyl 1-O-(2-trimethylsilylethyl) (2S)-pyrrolidine-1,2-dicarboxylate
• CAS: 132592-25-7
• 化学式: C₁₂H₂₃NO₄Si
• 分子量: 273.404
• InChiKey: ZGCCGYPMEMMCTK-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-1,2-pyrrolidinecarboxylic acid 1-(2-(trimethylsilyl)ethyl) 2-methyl diester 在 4-二甲氨基吡啶 、 硫酸 、 六正丁基二锡 、 (1S)-(+)-10-camphorsulfonic acid 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 19.5h， 生成 (2S,5S)-5-<(E)-1-<2-(methoxycarbonyl)ethenyl>>-1,2-pyrrolidinedicarboxylic acid 1-(2-(trimethylsilyl)ethyl) 2-methyl diester
  参考文献：
  名称：

  Electrochemical oxidation of proline derivatives: total syntheses of bulgecinine and bulgecin C

  摘要：

  The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.

  DOI：

  10.1021/jo00008a040
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 三乙胺 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成 (2S)-1,2-pyrrolidinecarboxylic acid 1-(2-(trimethylsilyl)ethyl) 2-methyl diester
  参考文献：
  名称：

  Comparison of enantioselective reductions using bead and monolith ‘disk’ polymer formulations of CBS catalysts

  摘要：

  Two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst were prepared and examined. Polymeric beads, with the auxiliary bound in pendant and crosslinked fashion, were prepared utilizing an improved procedure based upon earlier work. Optimization of a procedure for ketone reduction gives results that match those in solution. Attempted reuse gave mixed results. For comparison purposes, CBS functionalized monoliths were formed and tested but performed poorly. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.048

文献信息

• Electrochemical oxidation of proline derivatives: total syntheses of bulgecinine and bulgecin C
  作者：Anthony G. M. Barrett、Daniel Pilipauskas

  DOI：10.1021/jo00008a040

  日期：1991.4

  The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.
• Comparison of enantioselective reductions using bead and monolith ‘disk’ polymer formulations of CBS catalysts
  作者：Michael C. Varela、Seth M. Dixon、Michael D. Price、Jeffrey E. Merit、Patrick E. Berget、Saori Shiraki、Mark J. Kurth、Neil E. Schore

  DOI：10.1016/j.tet.2007.02.048

  日期：2007.4

  Two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst were prepared and examined. Polymeric beads, with the auxiliary bound in pendant and crosslinked fashion, were prepared utilizing an improved procedure based upon earlier work. Optimization of a procedure for ketone reduction gives results that match those in solution. Attempted reuse gave mixed results. For comparison purposes, CBS functionalized monoliths were formed and tested but performed poorly. (c) 2007 Elsevier Ltd. All rights reserved.