(+/-)-anti-2-(2-oxo-4,5-diphenyl-1-oxazolinyl)-3-hydroxyadipic acid 6-methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (+/-)-anti-2-(2-oxo-4,5-diphenyl-1-oxazolinyl)-3-hydroxyadipic acid 6-methyl ester
• 英文别名: (2S,3S)-3-hydroxy-6-methoxy-6-oxo-2-(2-oxo-4,5-diphenyl-1,3-oxazol-3-yl)hexanoic acid
• 化学式: C₂₂H₂₁NO₇
• 分子量: 411.411
• InChiKey: XPLYDQYWFUURCK-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+/-)-anti-2-(2-oxo-4,5-diphenyl-1-oxazolinyl)-3-hydroxyadipic acid 6-methyl ester 在 偶氮二甲酸二异丙酯 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 66.0h， 生成 (+/-)-N-((tert-butoxycarbonyl)(diethylphosphono)methyl)-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-(carbomethoxyethyl)azetidin-2-one
  参考文献：
  名称：

  Diastereoselective synthesis of the carbacephem framework

  摘要：

  A short, versatile, and diastereoselective method of preparing carbacephems has been developed. The procedure involves as a key step the aldol condensation of a protected glycine compound with a suitably designed aldehyde. In this step, most of the carbon skeleton of the carbacephem is assembled, and the two stereocenters of the final bicyclic beta-lactam are set. This step also provides well-placed and synthetically useful functionality for further elaboration into the desired target.

  DOI：

  10.1021/jo00055a013
• 作为产物：
  描述：

  4-戊烯酸甲酯 在 四(三苯基膦)钯 二甲基硫 、 O-苄基羟胺 、 臭氧 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (+/-)-anti-2-(2-oxo-4,5-diphenyl-1-oxazolinyl)-3-hydroxyadipic acid 6-methyl ester
  参考文献：
  名称：

  Diastereoselective synthesis of the carbacephem framework

  摘要：

  A short, versatile, and diastereoselective method of preparing carbacephems has been developed. The procedure involves as a key step the aldol condensation of a protected glycine compound with a suitably designed aldehyde. In this step, most of the carbon skeleton of the carbacephem is assembled, and the two stereocenters of the final bicyclic beta-lactam are set. This step also provides well-placed and synthetically useful functionality for further elaboration into the desired target.

  DOI：

  10.1021/jo00055a013

文献信息

• Diastereoselective synthesis of the carbacephem framework
  作者：Bruce T. Lotz、Marvin J. Miller

  DOI：10.1021/jo00055a013

  日期：1993.1

  A short, versatile, and diastereoselective method of preparing carbacephems has been developed. The procedure involves as a key step the aldol condensation of a protected glycine compound with a suitably designed aldehyde. In this step, most of the carbon skeleton of the carbacephem is assembled, and the two stereocenters of the final bicyclic beta-lactam are set. This step also provides well-placed and synthetically useful functionality for further elaboration into the desired target.