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Synthesis 2006(22): 3835-3840  
DOI: 10.1055/s-2006-950330
PAPER
© Georg Thieme Verlag Stuttgart · New York

Syntheses of 5-Fluoro and (E)-5-(2-Fluorovinyl) Arabinosyl Uridine Analogues­ as Potential Probes for the HSV-1 Thymidine Kinase Gene

Chung-Shan Yu*, Li-Wu Chiang, Chien-Hung Wu, Zhi-Kai Hsu, Ming-Hsun Lee, Si-Der Pan, Kai Pei
Department of Nuclear Sciences, National Tsing-Hua University, 101 Sec. 2, Guang-Fu Rd., Hsinchu 300, Taiwan
Fax: 886(3)5718649; e-Mail: csyu@mx.nthu.edu.tw;
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Publication History

Received 20 April 2006
Publication Date:
20 October 2006 (online)

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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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