Solid-Phase Synthesis of Glycosyl Phosphate Repeating Units via Glycosyl Boranophosphates as Stable Intermediates.

Solid-phase synthesis of glycosyl phosphate repeating units was investigated using glycosyl boranophosphates as stable precursors. The stable nature of glycosyl boranophosphate enables the elongation of a saccharide chain without remarkable decomposition. After deprotection of the boranophosphotriester linkages to boranophosphodiesters, the intersugar linkages were converted to the phosphate counterparts quantitatively using an oxaziridine derivative.

Solid-Phase Stereocontrolled Synthesis of Oligomeric P-Modified Glycosyl Phosphate Derivatives Using the Oxazaphospholidine Method.

Glycosyl phosphate repeating units can be found in the glycoconjugates of some bacteria and protozoa parasites. These structures and their P-modified analogs are attractive synthetic targets as antimicrobial, antiparasitic, and vaccine agents. However, P-modified glycosyl phosphates exist in different diastereomeric forms due to the chiral phosphorus atoms, whose configuration would highly affect their physiochemical and biochemical properties.