Syntheses of 5-fluoro and (E)-5-(2-fluorovinyl) arabinosyl uridine analogues as potential probes for the HSV-1 thymidine kinase gene

Abstract

The syntheses of 5-fluoro (FaraU) and (E)-5-(2-fluorovinyl) arabinosyl uridine (FVAU) via 5-trimethylstannyl and (E)-5-(2-tributylstannylvinyl) arabinosyl uridine analogues with select-fluor is described. Boc protection of the uridine moiety improved the yield of synthesis and differences between N-Boc and O-Boc isomers were established by 1H- and 13C NMR. The Boc-protected stannyl intermediates may be fluorinated with 18F to produce [18F]FaraU and [18F]FVAU. © Georg Thieme Verlag Stuttgart.