heptakis(2,3-di-O-allyl-6-deoxy-6-iodo)cyclomaltoheptaose | 145932-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptakis(2,3-di-O-allyl-6-deoxy-6-iodo)cyclomaltoheptaose
• CAS: 145932-45-2
• 化学式: C₈₄H₁₁₉I₇O₂₈
• 分子量: 2465.18
• InChiKey: KOQZCDHMNOCDNC-SAHBZSHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.81
• 重原子数：
  119.0
• 可旋转键数：
  49.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  258.44
• 氢给体数：
  0.0
• 氢受体数：
  28.0

反应信息

• 作为产物：
  描述：

  heptakis(2,3-di-O-allyl)-β-cyclodextrin 在 碘 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以56%的产率得到heptakis(2,3-di-O-allyl-6-deoxy-6-iodo)cyclomaltoheptaose
  参考文献：
  名称：

  Synthesis of a cycloheptaose consisting of (1 → 4)-linked 7-amino-6,7-dideoxy-α-d-gluco-heptopyranosyl units: A new analog of cyclomaltoheptaose

  摘要：

  Approaches to chain extension al the C-6 positions in cyclomaltoheptaose (1) were examined with the aim of producing novel beta-cyclodextrin analogs composed of heptose or hepturonic acid units. Iron carbonyl-mediated methoxycarbonylation, and nucleophilic displacement by cyanide, in the fully acetylated heptakis(6-deoxy-6-iodo) and heptakis(6-O-mesyl) derivates of 1, respectively, were unsuccessful, as were similar reactions attempted with the newly synthesized, analogous allyl-protected derivatives of 1. However, reaction of unprotected heptakis(6-deoxy-6-iodo)cyclomaltoheptaose with lithium cyanide in N,N-dimethylformamide afforded a high yield of the corresponding heptakis(6-cyano-6-deoxy) compound, namely, cyclohepta-(1 --> 4)-(6-deoxy-alpha-D-gluco-heptopyranosid)urononitrile, catalytic hydrogenation of which gave the title compound, cyclo-(1 --> 4)-(7-amino-6,7-dideoxy-alpha-D-glucoheptopyrano)heptaose, isolated as its peracetyl derivative.

  DOI：

  10.1016/0008-6215(92)80083-d