arabinonucleosides

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Abstract
The α‐D‐arabinonucleosides of cytosine (6) and 5‐fluorouracil (9) were prepared from the 2,3,‐5‐tri‐O‐benzoyl‐D‐arabinofuranosyl halides, in keeping with thetransrule. The 2′‐O‐methyl‐)3‐D‐arabinonucleosides of 5‐fluorouraeil (β‐14) and adenine (β‐21a) were prepared from 3,5‐di‐O‐(4‐ehlorobenzoyl)‐2‐O‐methyl‐α‐D‐arabinofuranosyl chloride, although in both cases a lesser amount of the α‐anomer was also found. Reaction of 3,5‐di‐O‐(4‐chlorobenzoyl)‐2‐deoxy‐2‐(methylthio)‐α‐D‐arabinofuranosyl chloride, prepared in four steps from methyl 2,3‐anhydro‐α‐D‐ribofurano‐side (15), withN‐benzoyladenine gave slightly more of the β‐ than the α‐arabinonucleoside20b. The β‐anomer was converted to 9‐[2‐deoxy‐2‐(methylthio)‐β‐D‐arabinofuranosyl]adenine. Only 1‐α‐D‐arabinofuranosylcytosine (6) proved to be cytotoxic.