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酰氯/1,4-二氮杂二环[2.2.2]辛烷促进的1,2:4,5-二-O-异亚丙基-D-呋喃果糖的缩醛迁移

Acyl chloride/DABCO-promoted acetal migration of 1,2:4,5-di-O-isopropylidene-D-fructopyranose.

作者信息

Meng Xiang-Bao, Li Yun-Feng, Li Zhong-Jun

机构信息

Department of Chemical Biology, School of Pharmaceutical Sciences, State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Science Center, Beijing 100083, PR China.

出版信息

Carbohydr Res. 2007 Jun 11;342(8):1101-4. doi: 10.1016/j.carres.2007.02.005. Epub 2007 Feb 13.

DOI:10.1016/j.carres.2007.02.005
PMID:17336949
Abstract

An unprecedented acetal migration was observed when 1,2:4,5-di-O-isopropylidene-D-fructose was treated with various acyl chlorides and 1,4-diaza-bicyclo[2.2.2]octane (DABCO). 2,3:4,5-Di-O-isopropylidene-D-fructose derivatives were isolated as the only product in high to quantitative yields. The acylium cations generated in situ were speculated as the electrophilic species to initiate the migration process.

摘要

当1,2:4,5-二-O-异亚丙基-D-果糖与各种酰氯和1,4-二氮杂双环[2.2.2]辛烷（DABCO）反应时，观察到了前所未有的缩醛迁移。2,3:4,5-二-O-异亚丙基-D-果糖衍生物作为唯一产物以高至定量的产率被分离出来。原位生成的酰基阳离子被推测为引发迁移过程的亲电物种。

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