Application of the hydrogenphosphonate approach in the synthesis of glycosyl phosphosugars linked through secondary hydroxyl groups

Article abstract of DOI:10.1016/0008-6215(90)84021-L

The hydrogenphosphonate approach has been used in syntheses of methyl α-D-mannopyranoside 2-, 3-, and 4-(α-D-mannopyranosyl phosphate), benzyl β-D-galactopyranoside 2-(α-D-mannopyranosyl phosphate), and methyl β-D-galactopyranoside 4-(α-D-mannopyranosyl phosphate).Condensation of 2,3,4,6-tetra-O-benzyl- or 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl hydrogenphosphonate with suitable, partially acylated monohydroxy derivatives in the presence of Me3CCOCl, followed by oxidation of the resulting hydrogenphosphonate diesters with iodine, gave the O-protected phosphate diesters in yields of 67-87percent.Deprotection then gave the glycosyl phosphosugars.