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Diisobutylaluminium Hydride (DIBAL-H) Promoted Secondary Rim Regioselective Demethylations of Permethylated beta-Cyclodextrin: A Mechanistic Proposal
Xiao, Sulong1,2; Yang, Ming2; Sinay, Pierre1; Bleriot, Yves1; Sollogoub, Matthieu1; Zhang, Yongmin1
关键词Cyclodextrins Dealkylation Reaction Mechanisms Regioselectivity Protecting Groups
刊名EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
2010-03-01
DOI10.1002/ejoc.200901230
8页:1510-1516
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Centre National de la Recherche Scientifique (CNRS) ; China Scholarship Council ; Centre National de la Recherche Scientifique (CNRS) ; China Scholarship Council
研究领域[WOS]Chemistry
关键词[WOS]DIFFERENTIATED ALPHA-CYCLODEXTRIN ; HETERO-BIFUNCTIONALIZATION ; SELECTIVE SYNTHESIS ; CROSS-LINKING ; DEBENZYLATION ; SUGARS ; FACE ; TRIISOBUTYLALUMINUM ; FUNCTIONALIZATION ; DERIVATIVES
英文摘要

Diisobutylaluminium hydride (DIBAL-H) promotes secondary rim regioselective bis-de-O-methylation at the 2(A)- and 3(B)-positions of permethylated beta-cyclodextrin. This result contrasts with the selective bis-de-O-benzylation of perbenzylated cyclodextrins in which regioselective deprotection occurs at the primary rim. To gain an insight into the mechanism of this remarkable contrasting behavior, the two corresponding permethylated cyclodextrins with an alcohol function at either the 2- or 3-position were synthesized. The cyclodextrin with the alcohol at the 3-position reacts with DIBAL-H to afford the 2(A) 3(B)-diol whereas the cyclodextrin with the alcohol at the 2-position is unreactive. This observation allows us to propose a mechanism for the demethylation reaction that involves for each demethylation step two molecules of aluminium reagent, in accord with the previous hypothesis on the debenzylation reaction. The second demethylation step appears to be faster than the first, the coordination of aluminium now being an intramolecular process.

语种英语
资助者Centre National de la Recherche Scientifique (CNRS) ; China Scholarship Council ; Centre National de la Recherche Scientifique (CNRS) ; China Scholarship Council
WOS记录号WOS:000275932600013
Citation statistics
Cited Times:23[WOS]   [WOS Record]     [Related Records in WOS]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/56505
Collection北京大学药学院
作者单位1.Univ Paris 06, Inst Parisien Chim Mol, CNRS, UMR 7201,FR2769, F-75005 Paris, France
2.Peking Univ, Hlth Sci Ctr, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100083, Peoples R China
Recommended Citation
GB/T 7714
Xiao, Sulong,Yang, Ming,Sinay, Pierre,et al. Diisobutylaluminium Hydride (DIBAL-H) Promoted Secondary Rim Regioselective Demethylations of Permethylated beta-Cyclodextrin: A Mechanistic Proposal[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2010(8):1510-1516.
APA Xiao, Sulong,Yang, Ming,Sinay, Pierre,Bleriot, Yves,Sollogoub, Matthieu,&Zhang, Yongmin.(2010).Diisobutylaluminium Hydride (DIBAL-H) Promoted Secondary Rim Regioselective Demethylations of Permethylated beta-Cyclodextrin: A Mechanistic Proposal.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(8),1510-1516.
MLA Xiao, Sulong,et al."Diisobutylaluminium Hydride (DIBAL-H) Promoted Secondary Rim Regioselective Demethylations of Permethylated beta-Cyclodextrin: A Mechanistic Proposal".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .8(2010):1510-1516.
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