Synthesis of two mono-deoxy β-cyclodextrin derivatives as useful tools for confirming DIBAL-H promoted bis-de-O-methylation mechanism |
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作者姓名: | Su Long Xiao De Min Zhou Ming Yang Fei Yu Li He Zhang Pierre Sinay Yong Min Zhang |
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作者单位: | State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China ; Institut Parisien de Chimie Moléculaire, UMR CNRS 7201, Université Pierre et Marie Curie-Paris 6, 4 place Jussieu, 75005 Paris, France ; Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, China |
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基金项目: | Financial support of this study from CNRS is gratefully acknowledged |
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摘 要: | Diisobutylaluminium hydride(DIBAL-H) promotes secondary rim regioselective bis-de-O-methylation of permethylatedβ-cyclodextrin (β-CD) to give diol 2.To gain an insight into the mechanism of this remarkable regioselective behavior,two corresponding permethylatedβ-CDs with an alcohol function at either 2- or 3-position were synthesized in our previous study.As a step further to this work,the two compounds were subjected to deoxygenation reaction with tributyltin hydride in the present of 2,2’- azobisisobutyronitrile affording the corresponding 2- and 3-deoxy permethylatedβ-CD derivatives(19 and 16).The structures of these two compounds were characterized by ID and 2D NMR and HRMS.Compounds 16 and 19 were unable to react with DIBALH which suggests that O-2~A and O-3~B are necessary for DIBAL-H promoted bis-de-O-methylation reaction of permethylatedβ-CD.
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关 键 词: | Cyclodextrin(CD) DIBAL-H Deoxy Synthesis Mechanism |
收稿时间: | 2012-09-21 |
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