Download PDF
Synlett 2000; 2000(1): 86-88
DOI: 10.1055/s-2000-6432
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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