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Communication | Regular issue | Vol 63, No. 12, 2004, pp.2719-2725
Published online, 26th October, 2004
DOI: 10.3987/COM-04-10218
Rapid Access to Glucopyranosyl-1,2,3-triazoles via Cu(I)-Catalyzed Reactions in Water

Rakesh A. Akula, David P. Temelkoff, Nicole D. Artis, and Peter Norris*

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

Abstract

1-Azido-1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose reacts with various terminal alkynes in the presence of CuSO4/ascorbic acid in water to give the corresponding 1,4-disubstituted 1,2,3-triazoles, which are isolated in high yield and purity by simply filtering the precipitate from the reaction mixture. Several sugar-derived acetylenes react similarly to yield triazole-linked disaccharide analogs.