bis-trehalo-3,3'-tetraethylene glycol | 133832-90-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis-trehalo-3,3'-tetraethylene glycol
• CAS: 133832-90-3
• 化学式: C₄₀H₇₂O₂₈
• 分子量: 1000.99
• InChiKey: AELQXJPNEDMIFT-UBFTXMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.57
• 重原子数：
  68.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  390.44
• 氢给体数：
  12.0
• 氢受体数：
  28.0

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 48.0h， 以65%的产率得到bis-trehalo-3,3'-tetraethylene glycol
  参考文献：
  名称：

  Chiral crown ethers incorporating .alpha.,.alpha.-trehalose. Unexpected structure of a trehalose containing 18-crown-6

  摘要：

  The reaction of 2,2'- (10), 3,2'- (11), and 3,3'-di-O-benzyl-4,6:4',6'-di-O-benzylidene-alpha,alpha-trehalose (12) with tetraethylene glycol ditosylate gave the corresponding chiral crowns mono-trehalo-3,3'- (1), bis-trehalo-3,3'- (3), mono-trehalo-2,3'- (5) and mono-trehalo-2,2'-tetraethylene glycol (7). The crystal structure of 1 was determined by X-ray analysis and the solution conformation of 1, 3, 5, and 7 by NMR spectroscopy and, in the case of 1, 3, and 7, molecular mechanics calculations. The geometry of the disaccharide moiety of 1,3, and 5 was as expected according to the exo anomeric effect. However, an unexpected conformation around the glycosidic linkage was found for the 18-crown-6 mono-trehalo-2,2'-tetraethylene glycol (7). This conformation can be accounted for by semiempirical calculations of possible intermediate dianionic structures.

  DOI：

  10.1021/jo00011a030