1',2,3,3',4,4'-hexa-O-benzyl-6'-O-(2-tert-butoxy-2-oxoethyl)-6-O-cyanomethylsucrose | 1415048-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1',2,3,3',4,4'-hexa-O-benzyl-6'-O-(2-tert-butoxy-2-oxoethyl)-6-O-cyanomethylsucrose
• CAS: 1415048-91-7
• 化学式: C₆₂H₆₉NO₁₃
• 分子量: 1036.23
• InChiKey: SHFOUFYJFHFNGH-WIJZKAMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.87
• 重原子数：
  76.0
• 可旋转键数：
  28.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  151.62
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  1',2,3,3',4,4'-hexa-O-benzyl-6'-O-(2-tert-butoxy-2-oxoethyl)-6-O-cyanomethylsucrose 在 lithium aluminium tetrahydride 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.17h， 生成 6,6'-[3-aza(4-methoxybenzyl)penta-1,5-di-yl]-1',2,3,3',4,4'-hexa-O-benzylsucrose
  参考文献：
  名称：

  Novel sucrose-based macrocyclic receptors for enantioselective recognition of chiral ammonium cations

  摘要：

  A new synthetic route to macrocyclic sucrose-based receptors with different substituents at the ring nitrogen atom is described. Very good enantioselectivity toward phenylethylammonium chloride was observed [a much stronger complex with the cation of the (S)-amine was formed] although the K-a values were low. Much higher K-a (1.4 x 10(4) M-1 in CDCI3/CD3OD) values of the complexes with aminoacid derivatives (especially valine) were found although this time the enantioselectivities were moderate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.003
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 6-O-(cyanomethyl)-1',2,3,3',4,4'-hexa-O-benzylsucrose 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 15.0h， 以93%的产率得到1',2,3,3',4,4'-hexa-O-benzyl-6'-O-(2-tert-butoxy-2-oxoethyl)-6-O-cyanomethylsucrose
  参考文献：
  名称：

  Novel sucrose-based macrocyclic receptors for enantioselective recognition of chiral ammonium cations

  摘要：

  A new synthetic route to macrocyclic sucrose-based receptors with different substituents at the ring nitrogen atom is described. Very good enantioselectivity toward phenylethylammonium chloride was observed [a much stronger complex with the cation of the (S)-amine was formed] although the K-a values were low. Much higher K-a (1.4 x 10(4) M-1 in CDCI3/CD3OD) values of the complexes with aminoacid derivatives (especially valine) were found although this time the enantioselectivities were moderate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.003