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Synthesis of the C-nucleoside, 5-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1-methyluracil, isosteric to the potent antiviral and anticancer nucleoside, 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1-methyluracil (2'-fluoro-5-methyl-ara-U or FMAU) was achieved by exploitation of the 4,5'-anhydro-nucleoside. Attempts at application of this ribosyl-to-arabinosyl pyrimidine transformation to 2,5'-anhydrouridine resulted in the formation of 2,2'-anhydro-5-substituted-arabinosyluracil.
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