methyl (((2R,4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)carbamoyl)-L-phenylalaninate | 1158857-91-0

• 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: methyl (((2R,4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)carbamoyl)-L-phenylalaninate
• CAS: 1158857-91-0
• 化学式: C₃₈H₄₀N₂O₈
• 分子量: 652.744
• InChiKey: JSJQQEWEJJPKBY-CTBSIUSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  113.58
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  N-((2R,4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-2,2,2-trichloroacetamide 、 L-苯丙氨酸甲酯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到methyl (((2R,4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)carbamoyl)-L-phenylalaninate
  参考文献：
  名称：

  Stereoselective Rearrangement of Trichloroacetimidates: Application to the Synthesis of α-Glycosyl Ureas

  摘要：

  A new method for the stereoselective synthesis of alpha-glycosyl ureas, via nickel-catalyzed [1,3]-rearrangement of glycosyl trichloroacetimidates, has been developed. The alpha-stereoselectivity at the anomeric carbon of the resulting trichloroacetamides depends on the nature of the cationic nickel catalyst. This method is applicable to a number of trichloroacetimidate substrates. The alpha-glycosyl trichloroacetamides can be directly converted into alpha-glycosyl ureas in the presence of amines. In all cases, the stereochemical integrity at the urea linkages remains intact.

  DOI：

  10.1021/ol900670a