A metal free aqueous route to 1,5-disubstituted 1,2,3-triazolylated monofuranosides and difuranosides

Abstract Vinyl sulfones and vinyl sulfone-modified carbohydrates were subjected to 1,3-dipolar-cycloaddition reactions with four different azidofuranosides having azido groups at the C5 and C6-positions under refluxing conditions in aqueous media without any metal catalyst to afford the 1,5-disubstituted 1,2,3-triazolylated monofuranosides and difuranosides in high yields. These syntheses of 1,5-disubstituted triazolylated monosaccharides as well as 1,5-disubstituted 1,2,3-triazole linked disaccharides open up a new possibility of connecting furanosides with a stable-triazole backbone. Download high-res image (55KB) Download full-size image