Phosphorylated sugars. Part 26. Synthesis of 3-deoxy-D-manno-oct-2-ulosonic acid 7-phosphate

Abstract

Of several phosphorylation methods tried, only that with bis(trichloroethyl) phosphorochloridate was satisfactory in producing the title compound starting either from methyl (methyl 8-O-benzyl-3-deoxy-4,5-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate or from methyl 4,8-di-O-benzyl-3-deoxy-α-D-manno-oct-2-ulopyranosidono-1,5-lactone. The synthesis of the phosphodiester methyl (methyl 3-deoxy-α-D-manno-oct-2-ulopyranosid)onate 7-(acetamidoethyl ammonium phosphate) is also described.