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  • Title: An unusual glycosylation product from a partially protected fucosyl donor under silver triflate activation conditions.
    Author: Daly R, Scanlan EM.
    Journal: Org Biomol Chem; 2013 Dec 28; 11(48):8452-7. PubMed ID: 24201894.
    Abstract:
    Partially protected glycosyl donors are extremely useful reagents for oligosaccharide synthesis allowing more facile deprotection and enhanced activity due to lower steric restraints. A partially protected fucosyl donor containing tert-butyldimethylsilyl (TBDMS) protecting groups was activated under bromine-silver triflate conditions in the presence of primary alcohols and found to give difucoside products exclusively, in good yield with excellent diastereoselectivity. The dimerisation reaction appears to require a conformational relaxation of steric crowding, induced upon activation of the glycosyl donor. The scope and limitations of this unusual glycosylation methodology are reported.
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