Optimised ‘click’ synthesis of glycopolymers with mono/di- and trisaccharides

Abstract

In this paper we investigate the optimum procedure for the post-polymerisation modification of alkyne-bearing polymer scaffolds with glycosyl azides. We first elaborate the one-pot synthesis of glycosyl azides, in aqueous solution, without the need for protecting groups and in multigram scale. Using these azides, the ligand tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) was shown to give the fastest kinetics for the ‘click’ reaction at ambient temperature, and was used to prepare homogenous oligosaccharide-modified glycopolymers. The terminal sugars of these oligosaccharides were used to introduce α-linked glucose which is typically synthetically challenging.