Synthesis of methyl (d-glycopyranosyl azide) uronates

Sodium hypochlorite oxidation catalysed by 2,2,6,6,-tetramethylpiperidine 1-oxide (TEMPO) is shown to be a mild and efficient approach to the title uronates. In the gluco, galacto, allo, and 2-acetamido-2-deoxy-gluco series, the corresponding β- or α- and β-glycosyl azides could be smoothly oxidised and alternative preparations are compared to this access.