Novel 2′-Deoxy PyrazineC-Nucleosides Synthesized VIA Palladium-Catalyzed Cross-Couplings
作者:
JohnA. Walker,
JiongJ. Chen,
JackM. Hinkley,
DeanS. Wise,
LeroyB. Townsend,
期刊:
Nucleosides and Nucleotides
(Taylor Available online 1997)
卷期:
Volume 16,
issue 10-11
页码: 1999-2012
ISSN:0732-8311
年代: 1997
DOI:10.1080/07328319708002550
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
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 pyrazineC-nucleosides and demonstrate the utility of a convergent approach for the synthesis of pyrazineC-nucleosides.
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