Fragments of bio-polymers containing glycosyl phosphate residues. 5. Synthesis of benzyl 2-O-and methyl 4-O-α-D)-mannosylphospho-β-D-galactosides and methyl 4-O-α-D-mannosylphospho-α-D)-glucoside by hydrogenphosphonate method
A. V. Nikolaev, I. A. Ivanova, V. N. Shibaev, N. K. Kochetkov
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: Hydrogenphosphonate approach was used successfully for the synthesis of (1-2)- and (l-4)-linked glycosyl phosphosugars, such as benzyl 2-O-α-D-mannopyranosylphospho-β-D-galactopyranoside, methyl 4-O-α-D-mannopyranosylphospho-β-D-galactopyranoside, and methyl 4-O-α-D-mannopyranosylphospho-α-D-glucopyranoside. They were obtained by glycosylphosphitylation of suitable partially acylated derivatives with 2,3,4,6-tetra-O-benzoyl- or 2,3,4,6-tetra-O-(3-benzoylpropionyl)-α-D-mannopyranosyl H-phosphonate in pyridine in the presence of trimethylacetyl chloride followed by oxidation with iodine and mild deacylation. The data of 1H, 13C, and 31P NMR spectra of the synthesized phosphate diesters are discussed.
Russian Journal of Bioorganic Chemistry 1990, 16 (8):1105-1117