Lewis Acid Catalysed Regioselective Access of Novel C‐2 Homo‐Pyranose Nucleosides From 2‐Acetoxy Methyl Glycals

Abstract

Novel C-2 homo-pyranose nucleosides can be synthesized by regioselective glycoconjugation of C-2 acetoxymethyl glycals with nucleobases in the presence of a catalytic amount of a Lewis acid. The reaction proceeded via the formation of exo-Ferrier allylic cation as an intermediate and the site selectivity is controlled on the basis of HSAB principle.