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  • Title: Glycal scavenging in the synthesis of disaccharides using mannosyl iodide donors.
    Author: Lam SN, Gervay-Hague J.
    Journal: J Org Chem; 2005 Mar 18; 70(6):2387-90. PubMed ID: 15760239.
    Abstract:
    [reaction: see text] High mannose glycans composed of alpha (1-->2) and alpha (1-->6) branched sugars are important components of the HIV-associated envelope glycoprotein, gp120. These substructures can be efficiently prepared in solution from glycosyl iodide precursors requiring only a slight excess of the iodide donor, which offers advantages over solid-phase methods that require more than 5 equiv of donor. During the reaction, excess iodide is converted to a glycal that is not easily separated from the desired disaccharide. To overcome this difficulty, a phase-trafficking methodology that relies upon nucleophilic interception of the 1,2 anhydrosugar resulting from oxidation of the glycal has been developed.
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