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■ Cu(I)-catalyzed Formation of D-Mannofuranosyl 1,4-Disubstituted 1,2,3-Triazolecarbohybrids

Penny L. Miner, Timothy R. Wagner, and Peter Norris*

*Department of Chemistry, Youngstown State University, 1 University Plaza, Youngstown, OH 44555-3663, U.S.A.

Abstract

2,3:5,6-Di-O-isopropylidene-D-mannofuranose has been exploited as a platform for the synthesis of new 1,2,3-triazolecarbohybrids. Placement of an azide group at C-1 (and C-6) of the carbohydrate allows for reaction with various alkynes in the presence of a Cu(I) catalyst to generate 1,4-disubstituted triazoles regiospecifically. The use of sugar-derived alkynes leads to 1,2,3-triazole-linked di- and trisaccharide carbohybrid analogs with retention of the β-D-manno configuration.