allyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(2,3-di-O-4-methoxybenzyl-4,6-O-4-methoxybenzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside | 181115-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(2,3-di-O-4-methoxybenzyl-4,6-O-4-methoxybenzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside
• CAS: 181115-77-5
• 化学式: C₆₃H₇₂O₁₇
• 分子量: 1101.25
• InChiKey: UCHXJGQGCAKJHF-DZNCEJSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.75
• 重原子数：
  80.0
• 可旋转键数：
  28.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  156.91
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(2,3-di-O-4-methoxybenzyl-4,6-O-4-methoxybenzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside 在 三乙烯二胺 、 RhCl(PPh₃)3 、 3 Angstroems MS 、 sodium cyanoborohydride 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 49.33h， 生成 2,3,6-tri-O-4-methoxybenzyl-4-O-(4-O-acetyl-2,3,6-tri-O-4-methoxybenzyl-α-D-glucopyranosyl)-D-glucopyranose
  参考文献：
  名称：

  Carbohydrate−Carbohydrate Interactions in Water with Glycophanes as Model Systems

  摘要：

  The synthesis and conformational properties of glycophanes 2 and 3 (cyclodextrin-cyclophane hybrid receptors containing two maltose units linked by (4-hydroxymethyl) benzoic acid spacer) are described. The binding properties in water of these receptors with a series of 4-nitrophenyl glycosides with alpha- and beta-configurations at the anomeric center have been studied using H-1 NMR spectroscopy and molecular mechanics calculations. A comparison of these properties with those of glycophane 1 (an alpha,alpha-trehalose containing glycophane) and alpha-cyclodextrin (alpha CD) using the same glycosides shows the existence of a stabilizing contribution to the free energy of binding in the case of of glycophanes but not in the case of the alpha CD system. This contribution is due to carbohydrate - carbohydrate interactions between both host and guest lipophilic sugar surfaces. Glycophanes 1, 2, and 3 show similar alpha/beta selectivity on binding the ligands, despite the great flexibility of 3 related to 1 and 2. Parallels are drawn between the thermodynamic behavior of these model systems and that proposed for sugar-protein interactions.

  DOI：

  10.1021/jo9807823
• 作为产物：
  描述：

  prop-2-en-1-yl-2,3,6-tri-O-acetyl-4-O-(α-D-2',3',4',6'-tetra-O-acetyl-glucopyranosyl)-β D-glucopyranoside 在 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 allyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(2,3-di-O-4-methoxybenzyl-4,6-O-4-methoxybenzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Carbohydrate−Carbohydrate Interactions in Water with Glycophanes as Model Systems

  摘要：

  The synthesis and conformational properties of glycophanes 2 and 3 (cyclodextrin-cyclophane hybrid receptors containing two maltose units linked by (4-hydroxymethyl) benzoic acid spacer) are described. The binding properties in water of these receptors with a series of 4-nitrophenyl glycosides with alpha- and beta-configurations at the anomeric center have been studied using H-1 NMR spectroscopy and molecular mechanics calculations. A comparison of these properties with those of glycophane 1 (an alpha,alpha-trehalose containing glycophane) and alpha-cyclodextrin (alpha CD) using the same glycosides shows the existence of a stabilizing contribution to the free energy of binding in the case of of glycophanes but not in the case of the alpha CD system. This contribution is due to carbohydrate - carbohydrate interactions between both host and guest lipophilic sugar surfaces. Glycophanes 1, 2, and 3 show similar alpha/beta selectivity on binding the ligands, despite the great flexibility of 3 related to 1 and 2. Parallels are drawn between the thermodynamic behavior of these model systems and that proposed for sugar-protein interactions.

  DOI：

  10.1021/jo9807823