TY - JOUR
T1 - Glycal scavenging in the synthesis of disaccharides using mannosyl iodide donors
AU - Lam, Son N.
AU - Gervay-Hague, Jacquelyn
PY - 2005/3/18
Y1 - 2005/3/18
N2 - (Chemical Equation Presented) High mannose glycans composed of α (1→2) and α (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.
AB - (Chemical Equation Presented) High mannose glycans composed of α (1→2) and α (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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U2 - 10.1021/jo0478609
DO - 10.1021/jo0478609
M3 - Article
C2 - 15760239
AN - SCOPUS:15444376696
VL - 70
SP - 2387
EP - 2390
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 6
ER -