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Synthesis of four mono-functionalized alpha-cyclodextrin derivatives for further confirming DIBAL-H-promoted bis-de-O-methylation mechanism
Xiao, Sulong1,2; Yang, Ming1; Yu, Fei1; Zhang, Lihe1; Zhou, Demin1; Sinay, Pierre2; Zhang, Yongmin2,3
关键词alpha-Cyclodextrin DIBAL-H Mechanism Synthesis
刊名TETRAHEDRON
2013-05-20
DOI10.1016/j.tet.2013.03.070
69期:20页:4053-4060
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
资助者CNRS ; University Pierre &amp ; Marie Curie (program of LIA) ; National Basic Research Program of China (973 Program) ; National Natural Science Foundation of China ; China Scholarship Council ; CNRS ; University Pierre &amp ; Marie Curie (program of LIA) ; National Basic Research Program of China (973 Program) ; National Natural Science Foundation of China ; China Scholarship Council
研究领域[WOS]Chemistry
关键词[WOS]PERMETHYLATED BETA-CYCLODEXTRIN ; UNAMBIGUOUS NMR ANALYSIS ; DIISOBUTYLALUMINUM HYDRIDE ; 3-HYDROXY ; SELECTOR
英文摘要

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.

语种英语
所属项目编号2010CB12300 ; 20932001 ; 20852001
资助者CNRS ; University Pierre &amp ; Marie Curie (program of LIA) ; National Basic Research Program of China (973 Program) ; National Natural Science Foundation of China ; China Scholarship Council ; CNRS ; University Pierre &amp ; Marie Curie (program of LIA) ; National Basic Research Program of China (973 Program) ; National Natural Science Foundation of China ; China Scholarship Council
WOS记录号WOS:000317810700004
引用统计
被引频次:5[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/67090
专题北京大学药学院
作者单位1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Univ Paris 06, CNRS UMR 7201, Inst Parisien Chim Mol, F-75005 Paris, France
3.Jianghan Univ, Inst Interdisciplinary Res, Wuhan Econ & Technol Dev Zone, Wuhan 430056, Peoples R China
推荐引用方式
GB/T 7714
Xiao, Sulong,Yang, Ming,Yu, Fei,et al. Synthesis of four mono-functionalized alpha-cyclodextrin derivatives for further confirming DIBAL-H-promoted bis-de-O-methylation mechanism[J]. TETRAHEDRON,2013,69(20):4053-4060.
APA Xiao, Sulong.,Yang, Ming.,Yu, Fei.,Zhang, Lihe.,Zhou, Demin.,...&Zhang, Yongmin.(2013).Synthesis of four mono-functionalized alpha-cyclodextrin derivatives for further confirming DIBAL-H-promoted bis-de-O-methylation mechanism.TETRAHEDRON,69(20),4053-4060.
MLA Xiao, Sulong,et al."Synthesis of four mono-functionalized alpha-cyclodextrin derivatives for further confirming DIBAL-H-promoted bis-de-O-methylation mechanism".TETRAHEDRON 69.20(2013):4053-4060.
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