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Synlett 2000; 2000(1): 86-88
DOI: 10.1055/s-2000-6432
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Synthesis of (E)-5-[2-(Tri-n-butylstannyl)vinyl] Substituted 2′-Deoxyuridine Derivatives for Use in Halogenation and Radiohalogenation Reactions

Chung-Shan Yu* , Franz Oberdorfer
  • *Department of Radiopharmaceutical Chemistry, German Cancer Research Center, Im Neuenheimer Feld 280, D-69120 Heidelberg, Germany; Fax +49 (62 21) 42 25 72; E-mail: C.Yu@DKFZ-Heidelberg.de
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Publication Date:
31 December 2000 (online)

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A facile synthesis is reported for 5-[2-(tri-n-butyl-stannyl)vinyl]-2′-deoxyuridine 1, starting from commercial 5-iodo-2′-deoxyuridine 2 via the stannylation reaction as the key step. The 3′,5′-di-O-acetyl-N(3)-p-toluoyl-protected analog of 1, compound 9, was then prepared. Electrophilic fluorination of 9 with carrier-added [18F]F2 provided the desired (E) and (Z) fluorovinyl compounds 10, but not as the major products. The E/Z ratio of 10 was 2 : 1. The main product of the reaction was the proton substituted compound 11.

terminal alkyne - stannylation - fluorodestannylation - radiohalogenation

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