(4S)-4-(1-methylethyl)-1,3-thiazolidine-2,3-dicarboxylic acid 3-(1,1-dimethylethyl) ester | 872051-66-6

• 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: (4S)-4-(1-methylethyl)-1,3-thiazolidine-2,3-dicarboxylic acid 3-(1,1-dimethylethyl) ester
• 英文别名: (4S)-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-propan-2-yl-1,3-thiazolidine-2-carboxylic acid
• CAS: 872051-66-6
• 化学式: C₁₂H₂₁NO₄S
• 分子量: 275.369
• InChiKey: VCPGUBLARLPCMY-VEDVMXKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-(1-methylethyl)-1,3-thiazolidine-2,3-dicarboxylic acid 3-(1,1-dimethylethyl) ester 、 (E)-N-benzylidenebenzylamine 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到(3S,4S,7S)-8-(tert-butoxycarbonyl)-7-(1-methylethyl)-3-phenyl-2-(phenylmethyl)-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：

  (2S)-2-(1-methylethyl)-cysteamine hydrochloride 在 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 31.0h， 生成 (4S)-4-(1-methylethyl)-1,3-thiazolidine-2,3-dicarboxylic acid 3-(1,1-dimethylethyl) 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

文献信息

• Asymmetric synthesis of 1,3-thiazolidine-derived spiro-β-lactams via a Staudinger reaction between chiral ketenes and imines
  作者：Giuseppe Cremonesi、Piero Dalla Croce、Francesco Fontana、Alessandra Forni、Concetta La Rosa

  DOI：10.1016/j.tetasy.2005.08.054

  日期：2005.10

  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.