cycloheptakis-(1->4)-2,6-di-O-hydroxypropyl-3-O-methyl-α-D-glucopyranosyl | 1344122-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cycloheptakis-(1->4)-2,6-di-O-hydroxypropyl-3-O-methyl-α-D-glucopyranosyl
• 英文别名: per(2,6-di-O-hydroxypropyl-3-O-methyl)-β-cyclodextrin
• CAS: 1344122-22-0
• 化学式: C₉₁H₁₆₈O₄₉
• 分子量: 2046.31
• InChiKey: SMWNKXXNXAITBG-CUVGCOKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.96
• 重原子数：
  140.0
• 可旋转键数：
  70.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  606.27
• 氢给体数：
  14.0
• 氢受体数：
  49.0

反应信息

• 作为产物：
  描述：

  per(2,6-di-O-allyl-3-O-methyl)-β-cyclodextrin 在 9λ²-borabicyclo[3.3.1]nonane 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以65%的产率得到cycloheptakis-(1->4)-2,6-di-O-hydroxypropyl-3-O-methyl-α-D-glucopyranosyl
  参考文献：
  名称：

  Regioselective allylation of cyclomaltoheptaose (β-cyclodextrin) leading to per(2,6-di-O-hydroxypropyl-3-O-methyl)-β-cyclodextrin

  摘要：

  The selective modification of cyclodextrins remains a real challenge to obtain well-defined structures. The targeted cycloheptakis-(1 -> 4)-2,6-di-O-hydroxypropyl-3-O-methyl-alpha-D-glucopyranosyl [per(2,6-di-O-hydroxypropyl-3-O-methyl)-beta-CD] was obtained by a three-step procedure. The selective allylation of the hydroxyl functions at the positions 2 and 6 was used as a first step. This reaction was revisited then enlarged to a and gamma-CDs to determine new conditions for a one-step synthesis in high yield. The per(2,6-di-O-allyl)-beta-CD derivative was then reacted with iodomethane to provide per(2,6-di-O-allyl-3-O-methyl)-beta-CD. Oxidative hydroboration of the allyl functions was then carried out in order to obtain a new CD derivative with seven primary hydroxyl functions on each side of the truncated cone, having a similar reactivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.033