2-Substituted derivatives of 9-.alpha.-D-arabinofuranosyladenine and 9-.alpha.-D-arabinofuranosyl-8-azaadenine

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Abstract
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-benzoyl-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.

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