3B-O-phenoxycarbonyl-per-O-methyl-α-cyclodextrin | 1430734-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3B-O-phenoxycarbonyl-per-O-methyl-α-cyclodextrin
• 英文别名: 3^B-O-phenoxycarbonyl-per-O-methyl-α-cyclodextrin
• CAS: 1430734-36-3
• 化学式: C₆₀H₉₈O₃₂
• 分子量: 1331.42
• InChiKey: DTHCHUHKBWCJBX-ZTWVEVBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  92.0
• 可旋转键数：
  25.0
• 环数：
  23.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  303.2
• 氢给体数：
  0.0
• 氢受体数：
  32.0

反应信息

• 作为产物：
  描述：

  硫代氯甲酸苯酯 、 2^I-VI,3^II-VI,6^I-VI-heptadeca-O-methylcyclomaltohexaose 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 10.0h， 生成 3B-O-phenoxythiocarbonyl-per-O-methyl-α-cyclodextrin 、 3B-O-phenoxycarbonyl-per-O-methyl-α-cyclodextrin
  参考文献：
  名称：

  Synthesis of four mono-functionalized α-cyclodextrin derivatives for further confirming DIBAL-H-promoted bis-de-O-methylation mechanism

  摘要：

  In our previous studies, a mechanism for DIBAL-H promoted regioselective bis-de-O-methylation of per-O-methylated cyclodextrin (CD) was proposed based on per-O-methylated beta-CDs. As a further step to this work, four per-O-methylated alpha-CD derivatives (6, 7, 11, and 18) with mono functional group at the secondary rim have been designed and synthesized. Using DIBAL-H as a chemical 'scalpel', we found that (1) only the O-methyl at C-2(A) of 6 could be easily removed and (2) the O-methyl at C-3(B) could be firstly regioselectively removed slowly, followed by a rapid removal of the second O-methyl at C-2(A) to provide 3. Combined with our previous studies, we think that not only O-3(B)-methyl but also O-2(A) and O-3(B) are necessary for the formation of 'tweezers' during DIBAL-H promoted bis-de-O-methylation reaction of per-O-methylated CD. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.070