Synthesis of pyridine-stretched 2′-deoxynucleosides

Russell Clayton, Michael L. Davis, William Fraser, Wei Li, Christopher A. Ramsden

Research output: Contribution to journalArticle

Abstract

Synthesis of novel pyridine-stretched nucleoside (PSN) analogues of adenine (strA) (1), 2,6-diaminopurine (strD) (15) and hypoxanthine (strH) (17) from 4(5)-nitroimidazole has been achieved. Glycosylation of 4(5)-nitroimidazole was optimized to give consistently good yields (>70%) of the desired analytically pure 5-nitro-1′-β isomer 8 which on hydrogenation, C-addition of ethoxymethylene malononitrile (EMMN) and cyclisation provides the key intermediate 14 for PSN synthesis.

Original languageEnglish
Pages (from-to)1483-1486
Number of pages4
JournalSynlett
Issue number9
Early online date17 Sep 2002
DOIs
Publication statusPublished - 2002

Keywords

  • 2′-deoxynucleosides
  • 5-aminoimidazoles
  • DNA - lin-pyridoadenosine
  • glycosylation
  • nucleoside analogues

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    Clayton, R., Davis, M. L., Fraser, W., Li, W., & Ramsden, C. A. (2002). Synthesis of pyridine-stretched 2′-deoxynucleosides. Synlett, (9), 1483-1486. https://doi.org/10.1055/s-2002-33505