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Improved synthesis of 2'-deoxy-2'-[18F]-fluoro-1-beta-D-arabinofuranosyl-5-iodouracil ([18F]-FIAU). 2010

Harry Anderson, and Nagavarakishore Pillarsetty, and Melchor Cantorias, and Jason S Lewis
Advion BioSystems, 19 Brown Road, Ithaca, NY 14850, USA.

An improved synthesis of 2'-[(18)F]-fluoro-2'-deoxy-1-beta-D-arabinofuranosyl-5-iodouracil ([(18)F]-FIAU) has been developed. The method utilizes trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed coupling of 2-deoxy-2-[(18)F]-fluoro-1,3,5-tri-O-benzoyl-d-arabinofuranose with 2,4-bis(trimethylsilyloxy)-5-iodouracil to yield the protected dibenzoyl-[(18)F]-FIAU. Dibenzoyl-[(18)F]-FIAU was deprotected with sodium methoxide to yield a mixture of alpha- and beta-anomers in a ratio of 1:1, which were purified by HPLC. The procedure described in this article eliminates the need for HBr activation of the sugar prior to coupling with silylated iodouracil and is suitable for automation. The total reaction time was about 110 min, starting from [(18)F]-fluoride. The average isolated yield of the required beta-anomer was 10+/-6% (decay corrected) with average specific activity of 125 mCi/micromol.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008698 Mesylates Organic salts or esters of methanesulfonic acid. Mesilate,Methanesulfonates,Mesilates,Mesylate,Methylenesulfonates
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D005462 Fluorine Radioisotopes Unstable isotopes of fluorine that decay or disintegrate emitting radiation. F atoms with atomic weights 17, 18, and 20-22 are radioactive fluorine isotopes. Radioisotopes, Fluorine
D001086 Arabinofuranosyluracil A pyrimidine nucleoside formed in the body by the deamination of CYTARABINE. Ara-U,Arabinosyluracil,Arauridine,Sponguridine,Uracil Arabinofuranoside,Uracil Arabinoside,1-beta-D-Arabinofuranosyl Uracil,NSC 68928,1 beta D Arabinofuranosyl Uracil,Ara U,Arabinofuranoside, Uracil,Arabinoside, Uracil,Uracil, 1-beta-D-Arabinofuranosyl
D014297 Trimethylsilyl Compounds Organic silicon derivatives used to characterize hydroxysteroids, nucleosides, and related compounds. Trimethylsilyl esters of amino acids are used in peptide synthesis. Compounds, Trimethylsilyl

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