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Synlett 2011(13): 1900-1904  
DOI: 10.1055/s-0030-1260943
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Novel 2-Cyano-7-deaza-8-azapurine- and 2-Cyano-8-azapurine-Derived Nucleosides

Philip Wainwright*a, Adrian Maddaforda, Michael Simmsa, Neil Forresta, Rebecca Glena, James Harta, Xiurong Zhanga, David C. Prydeb, Peter T. Stephensonb, Donald S. Middletonb, Thierry Guyotb, Scott C. Suttonc
a Peakdale Molecular Ltd., Peakdale Science Park, Sheffield Road, Chapel-en-le-frith, High Peak, SK23 0PG, UK
Fax: +44(1298)816701; e-Mail: phil.wainwright@peakdale.co.uk;
b Discovery Chemistry, Pfizer Global Research and Development, Ramsgate Road, Sandwich, CT13 9NJ, UK
c Pfizer Global Research and Development, 10770 Science Centre Drive, San Diego, CA 92121, USA
Further Information

Publication History

Received 30 March 2011
Publication Date:
14 July 2011 (online)

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Abstract

A novel systematic approach to the synthesis of 2-cyano-7-deaza-8-azapurine derived nucleosides is described. It is shown how this chemistry was developed with the labile 2-substituted nitrile position in mind, and also how the same approach is applicable to 2-cyano-8-azapurine derived nucleosides.

Key words

nucleosides - nitriles - protecting groups - heterocycles - glycosylation

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7

We have chosen the historical purine numbering system in this communication.