2-Substituted derivatives of 9-alpha-D-arabinofuranosyladenine were prepared via the fusion of tetra-O-acetyl-alpha-D-arabinofuranose with 2,6-dichloropurine followed by stepwise displacement of the chloro groups. A different approach, the reaction of 2,3,5-tri-O-benzoly-D-arabinofuranosyl bromide with 2,6-bis(methylthio)-8-azapurine in refluxing toluene in the presence of molecular sieve followed by stepwise reaction of the blocked nucleoside with methanolic ammonia and then other nucleophiles, gave 2-substituted derivatives of 9-alpha-D-arabinofuranosyl-8-azaadenine; In contrast to the parent compounds, none of these 2-substituted derivatives showed significant antiviral activity.