Improved synthesis of 2′-deoxy-2′-[18F]-fluoro-1-β-d-arabinofuranosyl-5-iodouracil ([18F]-FIAU) Journal Article

   


Authors: Anderson, H.; Pillarsetty, N.; Cantorias, M.; Lewis, J. S.
Article Title: Improved synthesis of 2′-deoxy-2′-[18F]-fluoro-1-β-d-arabinofuranosyl-5-iodouracil ([18F]-FIAU)
Abstract: An improved synthesis of 2'-[18F]-fluoro-2'-deoxy-1-β-d-arabinofuranosyl-5-iodouracil ([18F]-FIAU) has been developed. The method utilizes trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed coupling of 2-deoxy-2-[18F]-fluoro-1,3,5-tri-O-benzoyl-d-arabinofuranose with 2,4-bis(trimethylsilyloxy)-5-iodouracil to yield the protected dibenzoyl-[18F]-FIAU. Dibenzoyl-[18F]-FIAU was deprotected with sodium methoxide to yield a mixture of α- andβ-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 [18F]-fluoride. The average isolated yield of the required β-anomer was 10±6% (decay corrected) with average specific activity of 125 mCi/Μmol. © 2010 Elsevier Inc.
Keywords: unclassified drug; drug structure; drug synthesis; automation; kinetics; microfluidics; arabinofuranosyluracil; reliability; high performance liquid chromatography; tracer; catalysis; structure analysis; fluorine 18; pet; hsv1-tk; reaction time; fluorine radioisotopes; fiau; 2' deoxy 2' fluoro 1 beta dexto arabinofuranosyl 5 iodouracil f 18; deprotection reaction; drug purification; silylation; mesylates; trimethylsilyl compounds
Journal Title: Nuclear Medicine and Biology
Volume: 37
Issue: 4
ISSN: 0969-8051
Publisher: Elsevier Science Inc.  
Date Published: 2010-05-01
Start Page: 439
End Page: 442
Language: English
DOI: 10.1016/j.nucmedbio.2010.01.003
PUBMED: 20447555
PROVIDER: scopus
PMCID: PMC4410717
DOI/URL:

http://www.scopus.com/inward/record.url?eid=2-s2.0-77952551337&partnerID=40&md5=4fb600f1f6782a4baccbca8623856902
Notes: --- - "Export Date: 20 April 2011" - "CODEN: NMBIE" - "Source: Scopus"
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MSK Authors
  1. Nagavarakishore Pillarsetty
    132 Pillarsetty
  2. Melchor V Cantorias
    4 Cantorias
  3. Jason S Lewis
    456 Lewis
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