1',2,3,3',4,4'-hexa-O-benzyl-6,6'-(3-benzyl-3-azapenta-1,5-diyl)-sucrose | 865200-97-1

• 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-6,6'-(3-benzyl-3-azapenta-1,5-diyl)-sucrose
• 英文别名: 6,6'-(3-azabenzylpenta-1,5-di-yl)-1',2,3,3',4,4'-hexa-O-benzylsucrose；(1R,3S,4S,5R,6R,16R,17R,18S,19R)-11-benzyl-4,5,17,18,19-pentakis(phenylmethoxy)-3-(phenylmethoxymethyl)-2,8,14,20,21-pentaoxa-11-azatricyclo[14.3.1.13,6]henicosane
• CAS: 865200-97-1
• 化学式: C₆₅H₇₁NO₁₁
• 分子量: 1042.28
• InChiKey: SFVPEOCHDOWEEP-QNHGHQIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  77
• 可旋转键数：
  21
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1',2,3,3',4,4'-hexa-O-benzyl-6,6'-(3-benzyl-3-azapenta-1,5-diyl)-sucrose 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Macrocyclic receptors containing sucrose skeleton

  摘要：

  Crown ether analogues with incorporated sucrose unit were prepared by reaction of 1 ',2,3,3 ',4,4 '- hexa-O-benzylsucrose with polyethylene ditosylates in up to 52% yield. Stability constants of their complexes with Li+, Na+, K+, NH4+ were determined by the NMR titration method. The macrocycles were also tested as catalysts in the enantioselective Michael reaction, but with little success (ee up to only 22%). The macrocycle containing nitrogen in the ring was also prepared in good yield. All prepared macrocycles were easily converted into the free sucrose crowns (H-2/Pd/C) without destroying the (very labile) glycosidic bond. The crystal structure of the selected receptor was determined. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.046
• 作为产物：
  描述：

  6-O-(cyanomethyl)-1',2,3,3',4,4'-hexa-O-benzylsucrose 在 lithium aluminium tetrahydride 、 四丁基溴化铵 、 potassium carbonate 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.17h， 生成 1',2,3,3',4,4'-hexa-O-benzyl-6,6'-(3-benzyl-3-azapenta-1,5-diyl)-sucrose
  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