6,6'-bis-(O-2-iodoethyl)-1',2,3,3',4,4'-hexa-O-benzyl-sucrose | 865200-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-bis-(O-2-iodoethyl)-1',2,3,3',4,4'-hexa-O-benzyl-sucrose
• 英文别名: (2R,3R,4S,5R,6R)-2-(2-iodoethoxymethyl)-6-[(2S,3S,4R,5R)-5-(2-iodoethoxymethyl)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxolan-2-yl]oxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 865200-96-0
• 化学式: C₅₈H₆₄I₂O₁₁
• 分子量: 1190.95
• InChiKey: YUNKTGOQOJHPCS-TWVITFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.87
• 重原子数：
  71.0
• 可旋转键数：
  29.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101.53
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  6,6'-bis-(O-2-iodoethyl)-1',2,3,3',4,4'-hexa-O-benzyl-sucrose 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 74.0h， 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-benzylsucrose 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 13.5h， 生成 6,6'-bis-(O-2-iodoethyl)-1',2,3,3',4,4'-hexa-O-benzyl-sucrose
  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