New acyclic nucleoside analogues. Stereospecific synthesis of purines and pyrimidines substituted with chiral chains by sugar-ring opening of β-D-galactopyranosyl nucleosides

Abstract

2′,3′- and 3′,4′-Seco-nucleosides, retaining the carbon framework of β-D-ribofuranosyl nucleosides but having a hydroxymethyl substituent on the 4′ or 5′ position, have been synthesized and their antiviral properties examined. These hitherto unknown chiral acyclic nucleosides were stereospecifically prepared by ring opening of β-D-galactopyranosyl nucleosides by means of periodate oxidation followed by borohydride reduction. None of the prepared compounds showed marked antiviral effect against a variety of DNA and RNA viruses.