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  • Title: Pyranosides with 2,3-trans carbamate groups: exocyclic or endocyclic cleavage reaction?
    Author: Manabe S, Ito Y.
    Journal: Chem Rec; 2014 Jun; 14(3):502-15. PubMed ID: 24914008.
    Abstract:
    Pyranosides with 2,3-trans carbamate groups exhibit high 1,2-cis selectivity in glycosylation reactions. Using glycosyl donors with N-benzyl 2,3-trans carbamate groups, an anti-Helicobacter pylori oligosaccharide was synthesized in an efficient manner. Moreover, pyranosides with 2,3-trans carbamate groups readily undergo anomerization from the β to the α configuration under mild acidic conditions via endocyclic cleavage. Acyclic cations generated during the endocyclic cleavage reaction were captured using reduction and intramolecular Friedel-Crafts reaction. By exploiting this anomerization, multiply aligned 1,2-trans glycosyl bonds can be transformed to 1,2-cis glycosyl bonds in a single operation.
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