Carbohydrate Research 2010-01-01

Metal-mediated allylation of enzymatically oxidized methyl α-d-galactopyranoside

Ann-Sofie Leppänen, Outi Niittymäki, Kirsti Parikka, Maija Tenkanen, Patrik Eklund, Rainer Sjöholm, Stefan Willför, Ann-Sofie Leppänen, Outi Niittymäki, Kirsti Parikka, Maija Tenkanen, Patrik Eklund, Rainer Sjöholm, Stefan Willför

Index: Carbohydr. Res. 345 , 2610-5, (2010)

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Abstract

The C-6 unit of methyl α-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.Copyright © 2010 Elsevier Ltd. All rights reserved.