Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides

Seiji Masui, Yoshiyuki Manabe, Kohtaro Hirao, Atsushi Shimoyama, Takahide Fukuyama, Ilhyong Ryu, Koichi Fukase*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    6 Scopus citations

    Abstract

    Kinetically controlled Fischer glycosidation was achieved under flow conditions. β-Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) was used as an acid catalyst. This reaction directly converted aldohexoses into kinetically favored furanosides to enable the practical synthesis of furanosides. After optimization of the reaction temperature and residence time, glucofuranosides, galactofuranosides, and mannofuranosides were synthesized in good yields.

    Original languageEnglish
    Pages (from-to)397-400
    Number of pages4
    JournalSynlett
    Volume30
    Issue number4
    DOIs
    StatePublished - 1 Jan 2019

    Keywords

    • Fischer glycosidation
    • carbohydrate
    • flow chemistry
    • furanosides
    • kinetically controlled reaction
    • supported catalysis

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