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 (Glc N Ac). The synthesis of Glc N Ac analogues has been achieved through a straightforward approach starting from Glc N Ac-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 Glc N Ac-based drugs.