S. Nesnow, C. Heidelberger
Oct 1, 1973
Citations
0
Influential Citations
9
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
5-Fluoro-2-methoxypyridine (3) synthesized from 5-amino-2-methoxypyridine was converted to 4-benzyloxy-5-fluoro-2-methoxypyridine (12) and 2,4-dimethoxy-5-fluoropyridine (13) by a four step procedure employing the intermediate 5-fluoro-2-methoxy-4-nitropyridine N-oxide (7). Condensation of 3, 12, and 13 with 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide gave, after removal of the protecting groups, 4-deoxy-5-fluoro-3-deazauridine (20), 5-fluoro-3-deazauridine (23) and 5-fluoro-4-methoxy-3-deazauridine (25). Several alkylated and dealkylated derivatives of 3 and 12 were also prepared. Structure proof and anomeric configuration were determined from the uv, nmr, and CD data.