2,3,3',4,4'-hexa-O-benzyl-6,6'-O-ethoxyethylenesucrose | 392699-42-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,3',4,4'-hexa-O-benzyl-6,6'-O-ethoxyethylenesucrose
• 英文别名: (1R,3S,4S,5R,6R,16R,17R,18S,19R)-4,5,17,18,19-pentakis(phenylmethoxy)-3-(phenylmethoxymethyl)-2,8,11,14,20,21-hexaoxatricyclo[14.3.1.13,6]henicosane
• CAS: 392699-42-2
• 化学式: C₅₈H₆₄O₁₂
• 分子量: 953.139
• InChiKey: SLWMVXUUYONLAX-TWVITFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.03
• 重原子数：
  70.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  110.76
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3,3',4,4'-hexa-O-benzyl-6,6'-O-ethoxyethylenesucrose 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：

  1’,2,3,3’,4,4’-hexa-O-benzyl-6,6’-dichloro-6,6’-dideoxysucrose 在 咪唑 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 492.0h， 生成 2,3,3',4,4'-hexa-O-benzyl-6,6'-O-ethoxyethylenesucrose
  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

文献信息

• CROWN ETHER ANALOGS FROM SUCROSE
  作者：Mateusz Mach、Slawomir Jarosz、Arkadiusz Listkowski

  DOI：10.1081/car-100106931

  日期：2001.7.31

  A convenient synthesis of 1',2,3,3'4,4'-hexa-O-benzylsucrose (4) from the free disaccharide is presented. Diol 4 and previously obtained 1'-O-benzyloxymethyl-2,3,3',4,4'-penta-O-benzylsucrose (3) served as precursors for chiral crown ether analogs containing a sucrose backbone. Deprotection of macrocyclic compounds (removal of the benzyl blocks) was possible under hydrogenolysis conditions.