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Publication - Professor Roger Alder

    A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

    Citation

    Balmond, EI, Benito-Alifonso, D, Coe, DM, Alder, RW, McGarrigle, EM & Galan, MC, 2014, ‘A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides’. Angewandte Chemie - International Edition, vol 53., pp. 8190-8194

    Abstract

    A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.

    Full details in the University publications repository