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学科主题: 药学
题名:
Diisobutylaluminium Hydride (DIBAL-H) Promoted Secondary Rim Regioselective Demethylations of Permethylated beta-Cyclodextrin: A Mechanistic Proposal
作者: 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
发表日期: 2010-03-01
DOI: 10.1002/ejoc.200901230
期: 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
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
项目资助者: Centre National de la Recherche Scientifique (CNRS) ; China Scholarship Council
WOS记录号: WOS:000275932600013
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/56505
Appears in Collections:北京大学药学院_期刊论文

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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:
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.
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