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  • Methoxymethyl (MOM) group nitrogen protection of pyrimidines bearing C-6 acyclic side-chains
    Gazivoda, Tatjana ...
    Novel N-methoxymethylated (MOM) pyrimidine (4-13) and pyrimidine-2,4- diones (15-17) nucleoside mimetics in which an isobutyl side-chain is attached at theC-6 position of the pyrimidine moiety were ... synthesized. Synthetic methods via O-persilylated or N-anionic uracil derivatives have been evaluated for thesynthesis of N-1- and/or N-3- MOM pyrimidine derivatives with C-6 acyclic side-chains. A synthetic approach using an activated N-anionic pyrimidine derivative afforded the desired N,N-1,3-diMOM and N-1- MOM pyrimidines 4 and 5in good yield. Introduction of fluorine into the side-chain was performed with DAST as the fluorinating reagent to give a N,N-1,3-diMOM pyrimidine 13 with a 1-fluoro-3-hydroxyisobutyl moiety at C-6. Conformational study of the monotritylated N-1-MOM pyrimidine 12 by the use of the NOE experiments revealed the predominant conformation of the compound to be one where the hydroxymethyl group in the C-6 side-chain is close to the N-1-MOM moiety, while the OMTr is in proximity to the CH3-5 group. Contrary to this no NOE enhancements between the N-1-MOM group and hydroxymethyl or fluoromethyl protons in 13 were observed, which suggested a nonrestricted rotation along the C-6 side-chain. Fluorinated N,N-1,3-diMOM pyrimidine 13 emerged as a modelcompound for development of tracer molecules for non-invasive imaging of gene expression using positron emission tomography (PET).
    Vir: Molecules [Elektronski vir]. - ISSN 1420-3049 (Vol. 16, iss. 6, 2011, str. 5113-5129)
    Vrsta gradiva - članek, sestavni del
    Leto - 2011
    Jezik - angleški
    COBISS.SI-ID - 4698906

    Povezava(-e):

    http://www.mdpi.com/1420-3049/16/6/5113/pdf
    DOI

vir: Molecules [Elektronski vir]. - ISSN 1420-3049 (Vol. 16, iss. 6, 2011, str. 5113-5129)
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