Synthesis of 2-acetamido-2-deoxy-D)-glucose phosphate diesters, fragments of the capsular antigens of Escherichia coli K51 and Neisseria meningitidis X
A. V. Nikolaev, I. A. Ivanova, V. N. Shibaev
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: Hydrogenphosphonate method was used for synthesis of 4-nitrophenyl 2-acetamido-3-and 4-nitrophenyl 2-acetamido-4-(2-acetamido-2-deoxy-α-D-glucopyranosyl phosphate)-2-deoxy-β-D-glucopyranosides. The glycosides, phosphate diester fragments of the title bacteria capsular antigens, were obtained by H-phosphonylation of the suitably protected 2-acetamido-2-deoxy-β-D-grucopyranosides with 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-glucopyranosyl H-phosphonate in the presence of trimethylacetyl chloride followed by oxidation and deprotection.
Russian Journal of Bioorganic Chemistry 1990, 16 (12):1693-1695