heptakis(3-O-benzyl-2,6-di-O-methyl)-β-cyclodextrin | 129371-87-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptakis(3-O-benzyl-2,6-di-O-methyl)-β-cyclodextrin
• 英文别名: heptakis(3-O-benzyl-2,6-di-O-methyl)cyclomaltoheptaose
• CAS: 129371-87-5
• 化学式: C₁₀₅H₁₄₀O₃₅
• 分子量: 1962.25
• InChiKey: BKQGDGCJEIUNSN-KRCWNVGVSA-N

物化性质

• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  140.0
• 可旋转键数：
  42.0
• 环数：
  28.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  323.05
• 氢给体数：
  0.0
• 氢受体数：
  35.0

反应信息

• 作为反应物：
  描述：

  heptakis(3-O-benzyl-2,6-di-O-methyl)-β-cyclodextrin 在 对甲苯磺酸 作用下， 反应 48.0h， 以23%的产率得到Bn(-3)Glc2Me6Me(a1-4)[Bn(-3)]Glc2Me6Me(a1-4)[Bn(-3)]Glc2Me6Me(a1-4)[Bn(-3)]Glc2Me6Me(a1-4)[Bn(-3)]Glc2Me6Me(a1-4)[Bn(-3)]Glc2Me6Me(a1-4)[Bn(-3)]Glc2Me6Me
  参考文献：
  名称：

  Short Synthesis of Skeleton-Modified Cyclodextrin Derivatives with Unique Inclusion Ability

  摘要：

  [GRAPHICS]Skeleton-modified cyclodextrin (CD) derivatives, in which an alpha-(1,4)-glucosidic bond is converted into a beta-(1,4)-glucosidic bond, were conveniently synthesized by cleavage of a single glucosidic bond in permethylated and 2,6-di-O-methylated alpha- and beta-CDs and subsequent recyclization via the trichloroacetoimidate intermediates. The selective cleavage of an alpha-(1,4)-glucosidic bond of permethylated alpha- and beta-CDs was accomplished by stirring in 30% aq HClO4 at 25 degreesC to give the corresponding maltohexaose and maltoheptaose derivatives, respectively. The cleavage of a glucosidic bond of hexakis(3-O-benzyl-2,6-di-O-methyl)-alpha-CD was successfully carried out in a mixed 60% aq HClO4 and 1,4-dioxane solution (1:20). In the case of heptakis(3-O-benzyl-2,6-di-O-methyl)-beta-CD, the solvent-free reaction with beta-toluenesulfonic acid was found to be effective for selective cleavage of one glucosidic bond. The permethylated beta-CD derivative with a beta-(1,4)-glucosidic bond (4b) exhibited higher inclusion ability toward sodium m-nitrobenzoate than the parent permethylated beta-CD, while these hosts showed the same inclusion ability toward sodium p-nitrobenzoate. On the other hand, the beta-(1,4)-type permethylated alpha-CD derivative 4a exhibited lower inclusion ability toward sodium p- and m-nitrobenzoates than the parent permethylated alpha-CD. Interestingly, host molecules 4a and 4b showed inclusion selectivity for sodium m-nitrobenzoate as compared with the corresponding para-isomer, in contrast to permethylated CDs which possessed para-isomer selectivity. On the other hand, host molecules 4a and 4b showed para-isomer selectivity toward sodium nitrophenoxide guests, indicating that the inclusion selectivity was remarkably influenced by the guest hydrophilic groups. H-1 NMR studies on complexes of those beta-(1,4)-type CD derivatives with p- and m-nitrobenzoates and p- and m-nitrophenolates were carried out to estimate their structures.

  DOI：

  10.1021/jo048657g
• 作为产物：
  描述：

  溴甲苯 、 β-环糊精 、 碘甲烷 生成 heptakis(3-O-benzyl-2,6-di-O-methyl)-β-cyclodextrin
  参考文献：
  名称：

  A convenient preparation of per-2,6-di-O-methylcyclomalto-oligosaccharides

  摘要：

  DOI：

  10.1016/0008-6215(90)84214-f