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

    研究成果: Contribution to journalArticle査読

    6 被引用数 (Scopus)

    抄録

    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.

    本文言語英語
    ページ(範囲)967-983
    ページ数17
    ジャーナルHeterocycles
    79
    C
    DOI
    出版ステータス出版済み - 2009

    All Science Journal Classification (ASJC) codes

    • Analytical Chemistry
    • Pharmacology
    • Organic Chemistry

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