(2S,4R)-1,3-thiazolidine-2,4-dicarboxylic acid 4-methyl ester | 872051-57-5

• 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,4R)-1,3-thiazolidine-2,4-dicarboxylic acid 4-methyl ester
• 英文别名: 4-Methyl (2S,4R)-2,4-thiazolidinedicarboxylate；(2S,4R)-4-methoxycarbonyl-1,3-thiazolidine-2-carboxylic acid
• CAS: 872051-57-5
• 化学式: C₆H₉NO₄S
• 分子量: 191.208
• InChiKey: JMTJSXZQOAVFDE-IMJSIDKUSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  387.3±42.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.72
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1,3-thiazolidine-2,4-dicarboxylic acid 4-methyl ester 在 吡啶 、 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (3S,4R,7R)-8-benzoyl-7-methoxycarbonyl-3-phenyl-2-(phenylsulfonyl)-5-thia-2,8-diazaspiro[3,4]octan-1-one
  参考文献：
  名称：

  Asymmetric synthesis of 1,3-thiazolidine-derived spiro-β-lactams via a Staudinger reaction between chiral ketenes and imines

  摘要：

  Enantiomerically pure 1,3-thiazolidine-derived spiro-beta-lactams were stereoselectively synthesised by means of a Staudinger ketene-imine reaction starting from optically active N-Boc-1,3-thiazolidine-2-carboxylic acid derivatives and imines. The reactions were stereoselective and afforded spiro-beta-lactams with a relative trans-configuration. The absolute configuration of the new stereocentres was assigned on the basis of the well-accepted mechanism and confirmed by means of the X-ray crystal structure analysis. The spiro-beta-lactams were transformed into enantiomerically pure chiral monocyclic beta-lactams by opening the thiazolidine ring and recovering the chiral auxiliary. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.054
• 作为产物：
  描述：

  L-半胱氨酸甲酯盐酸盐 、 乙醛酸 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以64%的产率得到(2S,4R)-1,3-thiazolidine-2,4-dicarboxylic acid 4-methyl ester
  参考文献：
  名称：

  Asymmetric synthesis of 1,3-thiazolidine-derived spiro-β-lactams via a Staudinger reaction between chiral ketenes and imines

  摘要：

  Enantiomerically pure 1,3-thiazolidine-derived spiro-beta-lactams were stereoselectively synthesised by means of a Staudinger ketene-imine reaction starting from optically active N-Boc-1,3-thiazolidine-2-carboxylic acid derivatives and imines. The reactions were stereoselective and afforded spiro-beta-lactams with a relative trans-configuration. The absolute configuration of the new stereocentres was assigned on the basis of the well-accepted mechanism and confirmed by means of the X-ray crystal structure analysis. The spiro-beta-lactams were transformed into enantiomerically pure chiral monocyclic beta-lactams by opening the thiazolidine ring and recovering the chiral auxiliary. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.054