The in situ activation of thioglycosides with bromine: An improved glycosylation method

Jan O. Kihlberg, David A. Leigh, David R. Bundle

    Research output: Contribution to journalArticlepeer-review

    Abstract

    A one-step conversion of thioglycosides into 1,2-trans- or 1,2-cis-O-glycosides was accomplished, in situ, by treatment with bromine in the presence of a glycosyl acceptor and a promoter such as silver triflate or mercuric cyanide. This mild "one-pot" procedure gives O-glycosides in excellent yields with high stereochemical control, even with unreactive and hindered glycosyl acceptors. The reaction conditions are compatible with various protecting groups such as acetates, benzoates, benzyl ethers, N-phthalimido groups, and benzylidene acetals.
    Original languageEnglish
    Pages (from-to)2860-2863
    Number of pages3
    JournalJournal of Organic Chemistry
    Volume55
    Issue number9
    Publication statusPublished - 1990

    Fingerprint

    Dive into the research topics of 'The in situ activation of thioglycosides with bromine: An improved glycosylation method'. Together they form a unique fingerprint.

    Cite this