Novel 2′-Deoxy Pyrazine C-Nucleosides Synthesized VIA Palladium-Catalyzed Cross-Couplings

The palladium-catalyzed cross-couplings of 2-chloro-3,5-diamino-6-iodopyrazine (1a) and methyl 3-amino-6-iodopyrazine-2-carboxylate (1b) with 1,4-anhydro-3,5-O-bis[(tert-butyl)dimethylsilyl]-2-deoxy-D-erythro-pent-1-enitol (2) followed by desilylation and stereospecific reduction of the 2′-deoxy-3′-...

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Published inNucleosides & nucleotides Vol. 16; no. 10-11; pp. 1999 - 2012
Main Authors Walker, John A., Chen, Jiong J., Hinkley, Jack M., Wise, Dean S., Townsend, Leroy B.
Format Journal Article
LanguageEnglish
Published NEW YORK Taylor & Francis Group 01.10.1997
Marcel Dekker Inc
Subjects
Biochemistry & Molecular Biology
Life Sciences & Biomedicine
Science & Technology
REARRANGEMENT
HALIDES
ANOMERIC CONFIGURATION
METALATION
SPECTROSCOPY
VINYLATION
DIAZINES
GLYCALS
EFFICIENT
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Summary:The palladium-catalyzed cross-couplings of 2-chloro-3,5-diamino-6-iodopyrazine (1a) and methyl 3-amino-6-iodopyrazine-2-carboxylate (1b) with 1,4-anhydro-3,5-O-bis[(tert-butyl)dimethylsilyl]-2-deoxy-D-erythro-pent-1-enitol (2) followed by desilylation and stereospecific reduction of the 2′-deoxy-3′-keto adduct leads to the formation of 2-chloro-6-(2-deoxy-ß-D-ribofuranosyl)-3,5-diaminopyrazine (4a) and methyl 3-amino-6-(2-deoxy-ß-D-ribofuranosyl)pyrazine-2-carboxylate (4b) in 58% yield and 21% yield, respectively. These are the first syntheses of the heretofore unknown 2′-deoxy pyrazine C-nucleosides and demonstrate the utility of a convergent approach for the synthesis of pyrazine C-nucleosides.
ISSN:0732-8311
2332-3892
DOI:10.1080/07328319708002550