Synthesis of pyridine-stretched 2′-deoxynucleosides

Clayton, Russell; Davis, Michael L.; Fraser, William; Li, Wei and Ramsden, Christopher A. (2002). Synthesis of pyridine-stretched 2′-deoxynucleosides. Synlett (9), pp. 1483-1486.

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.

Publication DOI: https://doi.org/10.1055/s-2002-33505
Divisions: Life & Health Sciences > Pharmacy
Additional Information: Copyright 2011 Elsevier B.V., All rights reserved.
Uncontrolled Keywords: 2′-deoxynucleosides ,5-aminoimidazoles ,DNA - lin-pyridoadenosine ,glycosylation ,nucleoside analogues
Published Date: 2002

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