(2R,4S)-2-[(R)-Benzylcarbamoyl-(2-phenoxy-acetylamino)-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid | 66317-02-0

• 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: (2R,4S)-2-[(R)-Benzylcarbamoyl-(2-phenoxy-acetylamino)-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid
• CAS: 66317-02-0
• 化学式: C₂₃H₂₇N₃O₅S
• 分子量: 457.55
• InChiKey: WTWWOKGJXGYIPE-SVFBPWRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  116.76
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2-[(R)-Benzylcarbamoyl-(2-phenoxy-acetylamino)-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 、 2-氨基丁醇 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,4S)-2-[(1R)-2-(benzylamino)-2-oxo-1-[(2-phenoxyacetyl)amino]ethyl]-N-[(2R)-1-hydroxybutan-2-yl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide
  参考文献：
  名称：

  Stereoselective synthesis of a thiazolane amide using molecular recognition in the triazolyl-activated ester intermediate

  摘要：

  An amide derived from penicillin V and racemic (R/S)-2-aminobutanol was prepared with 83% de and shows significantly higher toxicity than the pure diastereomers prepared from homochiral 2-aminobutanol. This has been attributed to conformational changes in the resolved product brought about through hydrogen-bonded self-assembly in the intermediate. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.047
• 作为产物：
  描述：

  (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 1-ethyl-piperidine 、 苄胺 在 磷酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,4S)-2-[(R)-Benzylcarbamoyl-(2-phenoxy-acetylamino)-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Stereoselective synthesis of a thiazolane amide using molecular recognition in the triazolyl-activated ester intermediate

  摘要：

  An amide derived from penicillin V and racemic (R/S)-2-aminobutanol was prepared with 83% de and shows significantly higher toxicity than the pure diastereomers prepared from homochiral 2-aminobutanol. This has been attributed to conformational changes in the resolved product brought about through hydrogen-bonded self-assembly in the intermediate. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.047