Metal-mediated allylation of enzymatically oxidized methyl alpha-D-galactopyranoside

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Ann-Sofie Leppänen, Outi Niittymäki, Kirsti Parikka, Maija Tenkanen, Patrik Eklund, Rainer Sjöholm, Stefan Willför
Publisher: ELSEVIER SCI LTD
Publication year: 2010
Journal: Carbohydrate Research
Journal acronym: CARBOHYD RES
Volume number: 345
Issue number: 18
Start page: 2610
End page: 2615
Number of pages: 6
ISSN: 0008-6215


Abstract

The C-6 unit of methyl alpha-D-galactopyranoside was selectively modified by combining enzymatic oxidation with an indium-mediated allylation reaction The Barbier-Grignard type reaction where a carbonyl group reacts with an allyl halide proceeds in aqueous solution even with water as the only solvent thus carbohydrates can be modified without the need for drying or protection-deprotection steps The corresponding homoallyl alcohols are produced in high yields of >90% in the reactions with allyl bromide and cinnamyl chloride The main products were Isolated and characterized by GC-MS and NMR spectroscopy (C) 2010 Elsevier Ltd All rights reserved


Keywords

Allylation, Aqueous media, Indium mediated, Methyl alpha-D-galactopyranoside

Last updated on 2019-21-10 at 04:05