(2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-1,2-carboxylic acid 2-ethyl ester 1-vinyl ester | 193538-86-2

• 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,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-1,2-carboxylic acid 2-ethyl ester 1-vinyl ester
• 英文别名: 1-O-ethenyl 2-O-ethyl (2S,3R)-3-(methylsulfanylmethyl)pyrrolidine-1,2-dicarboxylate
• CAS: 193538-86-2
• 化学式: C₁₂H₁₉NO₄S
• 分子量: 273.353
• InChiKey: SUNZLHJIWLLFMK-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-1,2-carboxylic acid 2-ethyl ester 1-vinyl ester 在 盐酸 、 lithium hydroxide 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 28.5h， 生成 (2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-1,2-carboxylic acid 1-tert-butyl ester
  参考文献：
  名称：

  Asymmetric synthesis of (2S,3S)- and (2S,3R)-3-prolinomethionines: 3-methylsulfanylmethyl-pyrrolidine-2-carboxylic acids

  摘要：

  The synthesis of 3-prolinomethionine can be easily achieved in a diastereoselective and enantioselective way via zinc-enolate cyclisation. After transmetallation by CuCN.2LiCl, the zinc-copper derivative was reacted with S-methyl methanesulfonothioate leading in a ''one-pot'' procedure, to N-(alpha-methylbenzyl)-3-prolinomethionine benzyl ester. The alpha-methylbenzyl group was transformed in vinyl-oxycarbonyl and tertiobutyloxycarbonyl groups successively. Reprotonation of cis Voc prolinomethionine enolate at low temperature yielded the enantiomerically pure trans diastereoisomer. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00203-6
• 作为产物：
  描述：

  ethyl (S)-N-(but-3-en-1-yl)-N-(1-phenylethyl)glycinate 在 lithium chloride 、 zinc dibromide 、 lithium diisopropyl amide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 192.0h， 生成 (2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-1,2-carboxylic acid 2-ethyl ester 1-vinyl ester
  参考文献：
  名称：

  Asymmetric synthesis of (2S,3S)- and (2S,3R)-3-prolinomethionines: 3-methylsulfanylmethyl-pyrrolidine-2-carboxylic acids

  摘要：

  The synthesis of 3-prolinomethionine can be easily achieved in a diastereoselective and enantioselective way via zinc-enolate cyclisation. After transmetallation by CuCN.2LiCl, the zinc-copper derivative was reacted with S-methyl methanesulfonothioate leading in a ''one-pot'' procedure, to N-(alpha-methylbenzyl)-3-prolinomethionine benzyl ester. The alpha-methylbenzyl group was transformed in vinyl-oxycarbonyl and tertiobutyloxycarbonyl groups successively. Reprotonation of cis Voc prolinomethionine enolate at low temperature yielded the enantiomerically pure trans diastereoisomer. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00203-6

文献信息

• Asymmetric synthesis of (2S,3S)- and (2S,3R)-3-prolinomethionines: 3-methylsulfanylmethyl-pyrrolidine-2-carboxylic acids
  作者：Philippe Karoyan、Gérard Chassaing

  DOI：10.1016/s0957-4166(97)00203-6

  日期：1997.6

  The synthesis of 3-prolinomethionine can be easily achieved in a diastereoselective and enantioselective way via zinc-enolate cyclisation. After transmetallation by CuCN.2LiCl, the zinc-copper derivative was reacted with S-methyl methanesulfonothioate leading in a ''one-pot'' procedure, to N-(alpha-methylbenzyl)-3-prolinomethionine benzyl ester. The alpha-methylbenzyl group was transformed in vinyl-oxycarbonyl and tertiobutyloxycarbonyl groups successively. Reprotonation of cis Voc prolinomethionine enolate at low temperature yielded the enantiomerically pure trans diastereoisomer. (C) 1997 Elsevier Science Ltd.