Hubert Chapuis, T. Kubelka, Nicolas Joubert
Mar 1, 2012
Citations
0
Influential Citations
8
Citations
Journal
European Journal of Organic Chemistry
Abstract
Two approaches to the synthesis of the title 6-substituted 2(1H)-pyridon-3-yl C-2′-deoxyribonucleosides have been pursued. A protected 6-aminopyridine C-nucleoside intermediate was converted into the N-oxide followed by Ac2O-mediated rearrangement and final deprotection to give 6-acetylamino-2-oxo(1H)-pyridin-3-yl deoxyribonucleoside. Due to the unusually high stability of the N-acetyl group, the full deprotection was unsuccessful. In the second approach, 6-chloro-2-pyridone was converted into phosphorodiamidate, which underwent ortho-magnesiation and iodination to give the 3-iododerivative. It was then used in a Heck coupling with a sugar glycal and the resulting product deprotected to give 6-chloro-2-oxo(1H)-pyridin-3-yl deoxyribonucleoside, which was either directly or after reprotection converted into 6-methyl-, 6-amino-, and 6-unsubstituted pyridone C-nucleosides. The final nucleosides were very unstable and easily epimerized and/or oxidized, which limits (but not excludes) their further use in chemical biology.