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

• 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: (+/-)-anti-2-(2-oxo-4,5-diphenyl-1-oxazolinyl)-3-hydroxyadipic acid 1-allyl 6-methyl diester
• 英文别名: 6-O-methyl 1-O-prop-2-enyl (2S,3S)-3-hydroxy-2-(2-oxo-4,5-diphenyl-1,3-oxazol-3-yl)hexanedioate
• 化学式: C₂₅H₂₅NO₇
• 分子量: 451.476
• InChiKey: VQXKBSVTLSLPAP-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  102
• 氢给体数：
  1
• 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 1-allyl 6-methyl diester 在 四(三苯基膦)钯 O-苄基羟胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 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
• 作为产物：
  描述：

  4-戊烯酸甲酯 在 二甲基硫 、 臭氧 、 lithium diisopropyl amide 作用下， 反应 2.0h， 生成 (+/-)-anti-2-(2-oxo-4,5-diphenyl-1-oxazolinyl)-3-hydroxyadipic acid 1-allyl 6-methyl diester
  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.