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    Stereoselective α-Glycosylation with 3-O-Acetylated d-Gluco Donors
    Synlett (2006)
    Nikolay E. NifantievNadezhda E. UstyuzhaninaBozhena S. KomarovaNatalya S. ZlotinaVadim B. KrylovAlexey G. GerbstYury E. Tsvetkov
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    Abstract:
    The effect of a 3-O-acetyl group on the stereoselectivity of α-glycosylation with 2-O-benzylated d-gluco glycosyl donors was studied. It was shown that 3-O-acetylated donors gave α-anomers predominantly or exclusively, whereas glycosylation with the corresponding per-O-benzylated donors afforded mixtures of comparable amounts of α- and β-anomers. The higher α-stereoselectivity in the first case was accounted for by the remote anchimeric assistance of the 3-O-acetyl group, which was confirmed by theoretical calculations.
    Keywords:
    Glycosyl donor
    Chemoselectivity
    Topics:
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