Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement

Dayang Halimatulzahrah, bt. Abang Kamaluddin and Zainab, Ngaini (2011) Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement. Journal of Fundamental Sciences, 7 (2). pp. 93-96. ISSN 1823-626X

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Abstract

The reactions of 3,4,6-tri-O-acetyl-D-glucal with phenolic and aliphatic alcohol in various Lewis acid catalysts (namely La(NO3)3.6H2O, InCl3, ZnCl2 and BF3•OEt2) have furnished the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides via Ferrier rearrangement. BF3•OEt2 showed the best Lewis acids catalysts with excellent yields and minimum reaction times. The reactions performed in CH3CN gave better yields and shorter reaction times compared to CH2Cl2. The electron withdrawing properties of aromatic ring resulting lower yields of aryl 2,3-unsaturated glycopyranosides compared to alkyl 2,3-unsaturated glycopyranosides under this condition. This study is significant in the preparation of O-glycosides via Ferrier rearrangement

Item Type: Article
Uncontrolled Keywords: Ferrier rearrangement, Lewis acids, alcohols, glycosides, unimas, university, universiti, Borneo, Malaysia, Sarawak, Kuching, Samarahan, ipta, education, research, Universiti Malaysia Sarawak
Subjects: Q Science > QD Chemistry
Divisions: Academic Faculties, Institutes and Centres > Faculty of Resource Science and Technology
Depositing User: Karen Kornalius
Date Deposited: 15 Mar 2017 15:29
Last Modified: 15 Mar 2017 15:29
URI: http://ir.unimas.my/id/eprint/15583

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