title: Accessing C-1 phosphonylated 2-acylamino uronic acids via 2-nitro-glycals.
abstract: 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.
authors.affiliation: Institute for Glycomics, Griffith University, Gold Coast Campus, Queensland 4222, Australia.
authors.forename: Beenu
authors.initials: B
authors.lastname: Bhatt
authors.forename: Robin J
authors.initials: RJ
authors.lastname: Thomson
authors.forename: Mark
authors.initials: M
authors.lastname: von Itzstein
mesh_terms: D002244:Carbon / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D014574:Uronic Acids / Q000737:chemistry*
chemical_list: D009574:Nitro Compounds; D063065:Organophosphonates; D014574:Uronic Acids; D002244:Carbon