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

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

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    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
    Original languageUndefined/Unknown
    Pages (from-to)2610–2615
    Number of pages6
    JournalCarbohydrate Research
    Volume345
    Issue number18
    DOIs
    Publication statusPublished - 2010
    MoE publication typeA1 Journal article-refereed

    Keywords

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

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