hexakis(3-O-benzyl-2,6-di-O-methyl)-α-cyclodextrin | 129371-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexakis(3-O-benzyl-2,6-di-O-methyl)-α-cyclodextrin
• 英文别名: hexakis(3-O-benzyl-2,6-di-O-methyl)cyclomaltohexaose；(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31S,32R,33S,34R,35S,36R,37S,38R,39S,40R,41S,42R)-32,34,36,38,40,42-hexamethoxy-5,10,15,20,25,30-hexakis(methoxymethyl)-31,33,35,37,39,41-hexakis(phenylmethoxy)-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.23,6.28,11.213,16.218,21.223,26]dotetracontane
• CAS: 129371-86-4
• 化学式: C₉₀H₁₂₀O₃₀
• 分子量: 1681.92
• InChiKey: AAGDMLHLTLAIRF-HTSITQPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  120
• 可旋转键数：
  36
• 环数：
  28.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  277
• 氢给体数：
  0
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  hexakis(3-O-benzyl-2,6-di-O-methyl)-α-cyclodextrin 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 2.0h， 以92%的产率得到2,6-二-甲基-Alpha-环糊精
  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
• 作为产物：
  描述：

  溴甲苯 、 α-环糊精 、 碘甲烷 生成 hexakis(3-O-benzyl-2,6-di-O-methyl)-α-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

文献信息

• Short Synthesis of Skeleton-Modified Cyclodextrin Derivatives with Unique Inclusion Ability
  作者：Akira Kikuzawa、Toshiyuki Kida、Yohji Nakatsuji、Mitsuru Akashi

  DOI：10.1021/jo048657g

  日期：2005.2.1

  [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.
• TAKEO, KENICHI, CARBOHYDR. RES., 200,(1990) C. 481-485
  作者：TAKEO, KENICHI

  DOI：——

  日期：——
• A convenient preparation of per-2,6-di-O-methylcyclomalto-oligosaccharides
  作者：Kenichi Takeo

  DOI：10.1016/0008-6215(90)84214-f

  日期：1990.4