Synthesis of N-acetylglucosamine analogues modified at C6 position with azido-derived moieties

We report a simple synthetic scheme for the preparation of several azido-derived analogues of N-acetylglucosamine (GlcNAc). The synthesis of GlcNAc analogues has been achieved through a straightforward approach starting from GlcNAc-OMe via an intermediate C6 azido derivative. Products reported in this work were then obtained respectively by azido-alkyne cycloaddition reactions and reductive derivatizations of the same azido-intermediate. This synthetic pathway presents different possibilities of functionalization that can be exploited for the preparation of novel GlcNAc-based drugs. Graphical abstract: (Figure presented.)