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  • Title: Hydrolysis of alpha- and beta-glycosides. New experimental data and modeling of reaction pathways.
    Author: Deslongchamps P, Li S, Dory YL.
    Journal: Org Lett; 2004 Feb 19; 6(4):505-8. PubMed ID: 14961609.
    Abstract:
    [reaction: see text] The cyclization of oxocarbenium ion conformers 6alpha and 6beta (from 11E and 11Z) gave only the beta-glycoside 1beta, and the addition of methanol to the oxocarbenium ion 3 yielded mainly the alpha-glycoside 1alpha with both experiments being carried out under kinetically controlled conditions. RHF/6.31G calculations reproduce well these experimental results and show that the endocyclic and the exocyclic C-O bond cleavage processes can compete in the hydrolysis of 1beta, whereas 1alpha gets hydrolyzed by exocyclic C-O bond cleavage only.
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