New Acyclic Nucleoside Analogs - Stereospecific Synthesis Of Purines And Pyrimidines Substituted With Chiral Chains By Sugar-Ring Opening Of Beta-D-Galactopyranosyl Nucleosides

2',3'- and 3',4'-Seco-nucleosides, retaining the carbon framework of beta-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 beta-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.