(1R,3R,5R,10R,11S,12R,26S,27R,32R,34R)-8,29-diphenyl-11,34-bis(phenylmethoxy)-2,4,7,9,13,16,19,22,25,28,30,33-dodecaoxapentacyclo[24.7.1.03,12.05,10.027,32]tetratriacontane | 133832-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R,5R,10R,11S,12R,26S,27R,32R,34R)-8,29-diphenyl-11,34-bis(phenylmethoxy)-2,4,7,9,13,16,19,22,25,28,30,33-dodecaoxapentacyclo[24.7.1.03,12.05,10.027,32]tetratriacontane
• CAS: 133832-91-4
• 化学式: C₄₈H₅₆O₁₄
• 分子量: 856.964
• InChiKey: DWDLQWBKNKBONW-GWRBUOGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  62.0
• 可旋转键数：
  8.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129.22
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (1R,3R,5R,10R,11S,12R,26S,27R,32R,34R)-8,29-diphenyl-11,34-bis(phenylmethoxy)-2,4,7,9,13,16,19,22,25,28,30,33-dodecaoxapentacyclo[24.7.1.03,12.05,10.027,32]tetratriacontane 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 24.0h， 以94%的产率得到mono-trehalo-3,2'-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 、 3,2'-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43%的产率得到(1R,3R,5R,10R,11S,12R,26S,27R,32R,34R)-8,29-diphenyl-11,34-bis(phenylmethoxy)-2,4,7,9,13,16,19,22,25,28,30,33-dodecaoxapentacyclo[24.7.1.03,12.05,10.027,32]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

文献信息

• VICENT, C.;BOSSO, C.;CANO, F. H.;PAZ, J. L. G. DE;FOCES-FOCES, C.;JIMENEZ+, J. ORG. CHEM., 56,(1991) N1, C. 3614-3618
  作者：VICENT, C.、BOSSO, C.、CANO, F. H.、PAZ, J. L. G. DE、FOCES-FOCES, C.、JIMENEZ+

  DOI：——

  日期：——