S. Nesnow, C. Heidelberger
Oct 1, 1975
Citations
0
Influential Citations
3
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
4-Amino-5-fluoro-2-pyridone (4) [5-fluoro-3-deazacytosine] was isolated as the hydrochloride salt from the dealkylation of 4-amino-5-fluoro-2-methoxypyridine (2), which was obtained from the reduction of 5-fluoro-2-methoxy-4-nitropyridine-N-oxide (1). Acetylation of 2 gave 4-acetamido-5-fluoro-2-methoxypyridine (3), which was condensed with 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide to give the blocked nucleoside (8). Removal of the protecting groups gave 5-fluoro-3-deazacytidine. Fusion of the trimethylsilyl derivative of 4 (10), with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro pentofuranosyl chloride gave a mixture of the β and α-anomers 12 and 13, which were separated and deblocked to yield 5-fluoro-2′-deoxy-3-deazacytidine (14) and its α-anomer (15). Several alkylated and acetylated derivatives of 2 were prepared as model compounds for use in the proof of structure.