Glycosylation of 'basic' alcohols: methyl 6-(hydroxymethyl) picolinate as a case study

Shuai Wang, Dominique Lafont, Jani Rahkila, Benjamin Picod, Reko Leino, Sébastian Vidal

    Research output: Contribution to journalArticleScientificpeer-review

    6 Citations (Scopus)

    Abstract

    Glycosylation is promoted by acid promoters rendering the reactions with basic acceptors challenging. This report presents an in depth study involving methyl 6-(hydroxymethyl) picolinate as the model acceptor and 22 glycosyl donors to afford the desired glycosides in good yields ranging from 46% to 85%. Several parameters were evaluated, including the protecting groups of the glycosyl donor, the leaving group at the anomeric center, and the promoter. The influence of the pyridine ring was evident with a benzene-based acceptor affording high yields of glycoside (79%) in comparison to the pyridine-based acceptor (46%). The present work provides a general and reliable access to pyridine-containing glycosides. (C) 2013 Elsevier Ltd. All rights reserved.
    Original languageUndefined/Unknown
    Pages (from-to)35–46
    Number of pages12
    JournalCarbohydrate Research
    Volume372
    DOIs
    Publication statusPublished - 2013
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Carbohydrate
    • Glycoside
    • Glycosylation
    • Pyridine acceptor
    • Trichloroacetimidate

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