Tandem catalysis strategy for direct glycosylation of 1-hydroxy sugars. Methoxyacetic acid as an effective catalytic mediator

Yasuo Yokoyama, Takeshi Hanamoto, Shoko Suzuki, Kosuke Shimizu, Hiroshi Furuno, Junji Inanaga

    Research output: Contribution to journalArticlepeer-review

    6 Citations (Scopus)

    Abstract

    1-Hydroxy sugars were dehydratively coupled with a variety of alcohols including thiophenol in the presence of a catalytic amount of ytterbium(III) triflate [Yb(OTf)3] and methoxyacetic acid to give the corresponding glycosides in good to excellent yields, and in some cases, with high stereoselectivities. The reaction proceeds through selective esterification of 1-hydroxy sugars with methoxyacetic acid in the presence of free alcohols as glycosyl acceptors. The mechanism of methoxyacetic acid-mediated tandem catalysis with Yb(OTf)3 is discussed.

    Original languageEnglish
    Pages (from-to)967-983
    Number of pages17
    JournalHeterocycles
    Volume79
    Issue numberC
    DOIs
    Publication statusPublished - Jul 29 2009

    All Science Journal Classification (ASJC) codes

    • Analytical Chemistry
    • Pharmacology
    • Organic Chemistry

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