2^A-O-tert-butyldimethylsilyl-6^A-deoxy-S-phenyl-α-cyclodextrin | 599178-94-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2^A-O-tert-butyldimethylsilyl-6^A-deoxy-S-phenyl-α-cyclodextrin
• CAS: 599178-94-6
• 化学式: C₄₈H₇₈O₂₉SSi
• 分子量: 1179.28
• InChiKey: JRLHKTDLBNDBTC-NSCSZKOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.23
• 重原子数：
  79.0
• 可旋转键数：
  10.0
• 环数：
  23.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  443.67
• 氢给体数：
  16.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  2^A-O-tert-butyldimethylsilyl-6^A-deoxy-S-phenyl-α-cyclodextrin 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以56%的产率得到
  参考文献：
  名称：

  Mechanism of 2-O→3-O silyl migration in cyclomaltohexaose (α-cyclodextrin)

  摘要：

  To gain insight into the mechanism of the well-known 2-O-->3-O silyl migration of 2-O-silylated cyclomaltooligosaccharides (cyclodextrins) under basic conditions, we have undertaken studies of the reaction of 2(A)-O-TBDMSi-6(A)-deoxy-6(A)-S-phenyl-alpha-cyclodextrin with MeI and NaH. Under these conditions, the TBDMSi group on the C-2 oxygen was found to migrate onto the G oxygen in the glucose residue in which the C-2 oxygen is located, and not onto the C-3 oxygen in the adjacent glucose residue. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01149-3
• 作为产物：
  描述：

  mono-2-O-tert-butyldimethylsilyl-α-cyclodextrin 在 吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 生成 2^A-O-tert-butyldimethylsilyl-6^A-deoxy-S-phenyl-α-cyclodextrin
  参考文献：
  名称：

  Mechanism of 2-O→3-O silyl migration in cyclomaltohexaose (α-cyclodextrin)

  摘要：

  To gain insight into the mechanism of the well-known 2-O-->3-O silyl migration of 2-O-silylated cyclomaltooligosaccharides (cyclodextrins) under basic conditions, we have undertaken studies of the reaction of 2(A)-O-TBDMSi-6(A)-deoxy-6(A)-S-phenyl-alpha-cyclodextrin with MeI and NaH. Under these conditions, the TBDMSi group on the C-2 oxygen was found to migrate onto the G oxygen in the glucose residue in which the C-2 oxygen is located, and not onto the C-3 oxygen in the adjacent glucose residue. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01149-3