THE SYNTHESIS OF GLYCOSIDES OF 2-ACETAMIDO-2-DEOXYGLUCOSE CATALYZED BY MERCURIC IODIDE

Citation
Ae. Zemlyakov et al., THE SYNTHESIS OF GLYCOSIDES OF 2-ACETAMIDO-2-DEOXYGLUCOSE CATALYZED BY MERCURIC IODIDE, Bioorganiceskaa himia, 24(8), 1998, pp. 623-630
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
ISSN journal
01323423
Volume
24
Issue
8
Year of publication
1998
Pages
623 - 630
Database
ISI
SICI code
0132-3423(1998)24:8<623:TSOGO2>2.0.ZU;2-I
Abstract
The glycosylation of various alcohols with peracetylated alpha-D-gluco saminyl chloride catalyzed with mercuric iodide was studied along with the dependence of the reaction course on temperature, solvent, and qu antity of catalyst. At room temperature, only beta-glycosides of perac etylated N-acetylglucosamine were shown to result in dichloroethane or nitromethane with high yields, At 90-95 degrees C, anomerization was observed, which led to the corresponding a-glycosides. The possibility of the synthesis of disaccharides with the beta 1 --> 6 bond catalyze d by mercuric iodide was demonstrated.