The surprise synthesis of α-GlcNAc 1-C-sulfonates

Oxidation of GlcNAc thiazoline in the presence of an alcohol affords no glycosidation products, but rather the alkyl α-GlcNAc 1-C-sulfonate. E2 cleavage of the sulfonate ester and then O-deacetylation gives the α-GlcNAc 1-C-sulfonic acid, a new type of carbohydrate derivative.