An H -Phosphonate-Mediated Synthesis of Nucleotide-Pyranose Glycoconjugates

High Resolution Image Download MS PowerPoint Slide We explore a synthesis of nucleotide-pyranose conjugates, successfully developing an H -phosphonate-mediated coupling of pyranoses with nucleosides that favors making the reactive phosphorus(III) species within the pyranose (C6-OH or C1-OH) and affords, after oxidation to the free phosphate, glycoconjugates in good overall yields (65–84%). Following deprotection and final purification, the materials are evaluated in U87-MG and PANC-1 cells, with activities comparable to the parent drugs, indicating such conjugates worthy of deeper validation as prodrugs.