Accessing C-1 phosphonylated 2-acylamino uronic acids via 2-nitro-glycals

Article abstract of DOI:10.1021/jo2002193

Two approaches are described for the synthesis of 2-acylamino uronic acid glycosyl phosphonates from readily accessible d-glucal. The first approach that entailed oxidation of the C-6 hydroxyl group followed by phosphonylation of the uronate 2-nitro-glycal, resulted in the formation of the β-l-gulo- configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the β-d-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.