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  • Title: Differential reactivity of alpha- and beta-anomers of glycosyl acceptors in glycosylations. A remote consequence of the endo-anomeric effect?
    Author: Magaud D, Dolmazon R, Anker D, Doutheau A, Dory YL, Deslongchamps P.
    Journal: Org Lett; 2000 Jul 27; 2(15):2275-7. PubMed ID: 10930262.
    Abstract:
    When phenyl tri-O-benzyl-1-thio-beta-D-galactopyranosiduronic acid esters were coupled with a 1/1 mixture of alpha and beta 2,3 di-O-protected D-galactopyranosiduronic acid esters, the beta-anomer proved to be more reactive. Data from theoretical calculations suggested that the enhanced reactivity of this anomer compared with the alpha one would be due to a stronger hydrogen bond of the C-4 OH with the ring oxygen.
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