Development of a convenient route for the preparation of the N 2-Cbz-protected guaninyl synthon required for Boc-mediated PNA synthesis

Amelie Heuer-Jungemann, Nicola Marie Howarth, Saudatu C Ja’afaru, Georgina M. Rosair

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

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%. © 2013 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)6275-6278
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number46
Early online date19 Sep 2013
DOIs
Publication statusPublished - 13 Nov 2013

Keywords

  • Alkylation
  • Benzyloxycarbonyl protection
  • Guanin-9-yl synthon
  • Peptide nucleic acids
  • Selective synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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