Development of a convenient route for the preparation of the N2-Cbz-protected guaninyl synthon required for Boc-mediated PNA synthesis

[Display omitted] An efficient, high yielding, chemo- and regioselective, five-step synthetic route to N2-Cbz-guanin-9-yl acetic acid has been developed, which avoids the use of triphosgene. After formation of the N2-Boc protected purine from 2-amino-6-chloropurine, two successive base-controlled al...

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Bibliographic Details
Published in:Tetrahedron letters 2013-11, Vol.54 (46), p.6275-6278
Main Authors: Heuer-Jungemann, Amelie, Howarth, Nicola M., Ja’Afaru, Saudatu C., Rosair, Georgina M.
Format: Article
Language:English
Subjects:
Acetic acid
Alkylation
Analogue
Benzyloxycarbonyl protection
Dechlorination
Esters
Guanin-9-yl synthon
Monomers
Peptide nucleic acids
Selective synthesis
Synthesis (chemistry)
Tetrahedrons
X-rays
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Summary:[Display omitted] An efficient, high yielding, chemo- and regioselective, five-step synthetic route to N2-Cbz-guanin-9-yl acetic acid has been developed, which avoids the use of triphosgene. After formation of the N2-Boc protected purine from 2-amino-6-chloropurine, two successive base-controlled alkylations allowed an N9-tert-butyl acetate function followed by an N2-Cbz moiety to be installed. The selectivities of these reactions were confirmed through an X-ray crystallographic study of the 6-(2-nitrophenoxy) analogue. Final hydrolytic dechlorination and removal of the Boc and tert-butyl ester protecting groups were accomplished concomitantly under acidic conditions to afford the guanin-9-yl PNA monomer synthon in an overall yield of 53%.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.09.034