6,6'-bis-(O-2-hydroxyethyl)-1',2,3,3',4,4'-hexa-O-benzyl-sucrose | 865200-95-9

• 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-hydroxyethyl)-1',2,3,3',4,4'-hexa-O-benzyl-sucrose
• 英文别名: 2-[[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5R)-5-(2-hydroxyethoxymethyl)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxolan-2-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]ethanol
• CAS: 865200-95-9
• 化学式: C₅₈H₆₆O₁₃
• 分子量: 971.154
• InChiKey: CJUBLFBVGNNROD-TWVITFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.98
• 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：
  141.99
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  6,6'-bis-(O-2-hydroxyethyl)-1',2,3,3',4,4'-hexa-O-benzyl-sucrose 在 4-二甲氨基吡啶 、 sodium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 56.0h， 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：

  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 sodium hydroxide 、 lithium aluminium tetrahydride 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 7.0h， 生成 6,6'-bis-(O-2-hydroxyethyl)-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

文献信息

• Synthesis and complexation properties towards the ammonium cation of aza-coronand analogues containing sucrose
  作者：Slawomir Jarosz、Bartosz Lewandowski

  DOI：10.1016/j.carres.2008.01.016

  日期：2008.4

  1',2,3,3',4,4'-Hexa-O-benzyl-sucrose was converted in good yields into the macrocyclic receptors containing two and three nitrogen atoms in the ring. Their complexation properties towards the ammonium cation were significantly higher than for receptors without any nitrogen atoms in the ring.

  1'，2,3,3'，4,4'-Hexa-O-苄基蔗糖以高收率转化为在环中包含两个和三个氮原子的大环受体。它们对铵阳离子的络合特性显着高于环中没有任何氮原子的受体。