An investigation on stereospecific fluorination at the 2'-arabino-position of a pyrimidine nucleoside: radiosynthesis of 2'-deoxy-2'-[(18)F]fluoro-5-methyl-1-β-D-arabinofuranosyluracil.

Direct fluorination at the 2'-arabino-position of a pyrimidine nucleoside has been a long-standing challenge, yet we recently reported such a stereospecific fluorination for the first time in the synthesis of [(18)F]FMAU, albeit in low yields. Herein we report the results of an investigation on stereospecific fluorination on a variety of precursors for synthesis of [(18)F]FMAU. Several precursors were synthesized in multiple steps and fluorination was performed at the 2'-arabino position using K[(18)F]/kryptofix 2.2.2. All precursors produced [(18)F]FMAU in low yields.