2^I-VI,3^II-VI,6^I-VI-heptadeca-O-methylcyclomaltohexaose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2^I-VI,3^II-VI,6^I-VI-heptadeca-O-methylcyclomaltohexaose
• 英文别名: 3^B-hydroxyl-per-O-methyl-α-cyclodextrin；mono-3-hydroxy-per-O-methyl-α-cyclodextrin；(1S,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31S,32R,33S,34R,35S,36R,37S,38R,39S,40R,41S,42R)-32,33,34,35,36,37,38,39,40,41,42-undecamethoxy-5,10,15,20,25,30-hexakis(methoxymethyl)-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]dotetracontan-31-ol
• 化学式: C₅₃H₉₄O₃₀
• 分子量: 1211.31
• InChiKey: HRIKVFLIEIPOHW-XVQKRXOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  83
• 可旋转键数：
  23
• 环数：
  22.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  288
• 氢给体数：
  1
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  2^I-VI,3^II-VI,6^I-VI-heptadeca-O-methylcyclomaltohexaose 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 2^A,3^B-dihydroxyl-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
• 作为产物：
  描述：

  2^A,3^B-dihydroxyl-per-O-methyl-α-cyclodextrin 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以78%的产率得到2^I-VI,3^II-VI,6^I-VI-heptadeca-O-methylcyclomaltohexaose
  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

文献信息

• Direct and convenient access to mono 3-hydroxy per-O-methylated α-cyclodextrin
  作者：Thomas Chaise、Eric Bourgeaux、Pascal Cardinael、J.C Combret

  DOI：10.1016/j.tetlet.2004.06.003

  日期：2004.7

  A direct way to reach mono 3-hydroxy per-O-methylated alpha-cyclodextrin by de-beta-methylation with phenylthiotrimethylsilane is reported. This compound is fully characterized by NMR spectroscopy and liquid chromatography with mass spectroscopy coupling. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of four mono-functionalized α-cyclodextrin derivatives for further confirming DIBAL-H-promoted bis-de-O-methylation mechanism
  作者：Sulong Xiao、Ming Yang、Fei Yu、Lihe Zhang、Demin Zhou、Pierre Sinaÿ、Yongmin Zhang

  DOI：10.1016/j.tet.2013.03.070

  日期：2013.5

  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.