1-((2R,4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-3-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-2-yl)methyl)urea | 1158857-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((2R,4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-3-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-2-yl)methyl)urea
• CAS: 1158857-88-5
• 化学式: C₆₂H₆₄N₂O₁₂
• 分子量: 1029.2
• InChiKey: NGKUBTOEFNFWMD-IPOITMSQSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.86
• 重原子数：
  76.0
• 可旋转键数：
  22.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  142.66
• 氢给体数：
  2.0
• 氢受体数：
  12.0

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 、 ((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-2-yl)methanamine 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到1-((2R,4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-3-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-2-yl)methyl)urea
  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