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 selectfluor 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.

Key words

stannane - fluoro - arabinosyl - cancer - gene therapy

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