| 133832-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• CAS: 133832-89-0
• 化学式: C₉₆H₁₁₂O₂₈
• 分子量: 1713.93
• InChiKey: VMILCKFAXDDEOF-IDWNLDLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.37
• 重原子数：
  124.0
• 可旋转键数：
  16.0
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  258.44
• 氢给体数：
  0.0
• 氢受体数：
  28.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 2,2'-di-O-benzyl-4,6:4',6'-di-O-benzylidene-α,α-trehalose 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 以15%的产率得到(1R,3R,5R,10R,11S,25S,26R,31R,33R,34R)-8,28-diphenyl-33,34-bis(phenylmethoxy)-2,4,7,9,12,15,18,21,24,27,29,32-dodecaoxapentacyclo[23.7.1.13,11.05,10.026,31]tetratriacontane
  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