Title: A Convenient Route for the Synthesis of 3-Deazaspongosine
Authors: Bande, Omprakash
Herdewijn, Piet # ×
Issue Date: 2014
Publisher: Wiley-VCH
Series Title: European Journal of Organic Chemistry vol:2014 issue:1 pages:231-236
Abstract: The first chemical synthesis of the 3-deazaspongosine nucleoside is described, starting from commercially available 4-amino-2,6-dichloropyridine. The key step is the introduction of required functional groups at the 2 and 6 positions of the 4-amino-3-nitropyridine without any conflict in the synthesis of nucleobase. Regioselective nucleophilic substitution with allyl alkoxide at the 2 position of 4-amino-2,6-dimethoxypyridine, followed by sequential deallylation and chlorination led to the desired 2-chloro derivative. Ring closure of the 3,4-diamino pyridine and stereoselective glycosylation of the
imidazo[4,5-c]pyridine with tetraacetate-protected ribofuranose gave only the N9-β-isomer. A final nucleophilic displacement of the 6-chloride by hydrazine followed by reduction with Raney Nickel gave the desired 3-deazaspongosine.
ISSN: 1434-193X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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