A metal-free route towards 1,5-disubstituted 1,2,3-triazolylmethylene linked disaccharides: Synthesis in a biodegradable hydroxyl-ammonium-based aqueous ionic liquid media

Abstract

Suitably protected carbohydrates were joined together using 1,5-disubstituted 1,2,3-triazolylmethylene (1,5-DTM) linkers. The DTM linker was built by the 1,3-dipolar cycloaddition reactions of a series of sugar azides with vinyl sulfonylmethylene-modified furanose or pyranose under metal free conditions. Three different biodegradable hydroxylammonium based ionic liquids were studied in water as the reaction media. The N,N-dimethyl ethanolammonium formate-water mixture was found to be the best reaction medium because the reaction time was shortened considerably to generate a dozen new 1,5-DTM-linked disaccharides.