mono-2-O-tert-butyldimethylsilyl-α-cyclodextrin | 441764-43-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono-2-O-tert-butyldimethylsilyl-α-cyclodextrin
• 英文别名: 2A-O-[(1,1-Dimethylethyl)dimethylsilyl]-|A-Cyclodextrin；(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31R,32R,33R,34R,35R,36R,37R,38R,39R,40R,41S,42R)-42-[tert-butyl(dimethyl)silyl]oxy-5,10,15,20,25,30-hexakis(hydroxymethyl)-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-31,32,33,34,35,36,37,38,39,40,41-undecol
• CAS: 441764-43-8
• 化学式: C₄₂H₇₄O₃₀Si
• 分子量: 1087.12
• InChiKey: VNNAMTRSPBCPJV-MYHQYEFTSA-N

物化性质

• 沸点：
  1312.5±65.0 °C(Predicted)
• 密度：
  1.64±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -10.03
• 重原子数：
  73.0
• 可旋转键数：
  8.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  463.9
• 氢给体数：
  17.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 α-环糊精 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 mono-2-O-tert-butyldimethylsilyl-α-cyclodextrin 、 (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31R,32R,33R,34R,35R,36R,37R,38R,39R,40R,41R,42R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-10,15,20,25,30-pentakis(hydroxymethyl)-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-31,32,33,34,35,36,37,38,39,40,41,42-dodecol
  参考文献：
  名称：

  Regioselective silylation of C-2 hydroxyl group of α-cyclodextrin dependent on reaction temperature

  摘要：

  Silylations of the C-2 hydroxyl group of a-cyclodextrin were carried out using t-butyldimethylsilyl imidazole in the presence of 4 Angstrom molecular sieves in N,N-dimethylformamide. A unique aspect of this silylation method is the temperature dependence of the regioselectivity. sitylation at 0degreesC regioselectively favored the C-6 position to afford mono-6-O-t-butyldimethylsilyl-alpha-cyclodextrin, whereas silylation at 140degreesC exhibited high regioselectivity on the C-2 hydroxyl group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00258-7