Efficient synthesis of 5-(β-D-ribofuranosyl)nicotinamide and its α-isomer Journal Article
| Authors: | Pankiewicz, K. W.; Sochacka, E.; Kabat, M. M.; Ciszewski, L. A.; Watanabe, K. A. |
| Article Title: | Efficient synthesis of 5-(β-D-ribofuranosyl)nicotinamide and its α-isomer |
| Abstract: | Condensation of 2,3-O-isopropylidene-5-O-(tetrahydropyranyl)-D-ribonolactone (3) with 3-cyano-5-lithiopyridine afforded 1-(3-cyanopyridin-5-yl)-2,3-O-isopropylidene-5-O-(tetrahydropyranyl)-β-D-ribofuran-1-ulose (5a), which was reduced with NaBH4 to a 1:1 allo/altro mixture of 5-[2,3-O-isopropylidene-5-O-(tetrahydropyranyl)-Dpentitol-1-yl]-3-cyanopyridine (7a). The isomers were chromatographically separated. Treatment of allo-7a with TsOH/MeOH gave 5-(2,3-O-isopropylidene-D-allo-pentitol-1-yl)-3-cyanopyridine (allo-8a), which was acetonated to give 5-(2,3:4,5-di-O-isopropylidene-D-o(Zo-pentitol-1-yl)-3-cyanopyridine (allo-9a). Mesylation of allo-9a to allo-10 followed by acid hydrolysis with CF3CO2H/CHCl3 afforded 5-(α-D-ribofuranosyl)-3-cyanopyridine (11a). The β-isomer la was synthesized in a similar manner from altro-7a. Inversion of the configuration at the C-1 position of 6-(2,3:4,5-di-O-isopropylidene-D-allo-pentitol-1-yl)-2-bromopyridine (allo-9b) into the corresponding altro isomer altro-9b was achieved albeit in modest yield (24%) by mesylation of allo-9b to allo-10b followed by treatment with potassium superoxide. Interconversion of altro-9a or -9b into the corresponding allo derivatives was readily achieved in excellent yield by oxidation with CrO3/pyridine/Ac2O to the corresponding keto intermediates 19 followed by borohydride reduction. Treatment of the 1-O-mesylate allo-10b with NaN3 in DMF afforded the corresponding 1-azido-1-deoxy altro derivative (17). Similar treatment of the 1-O-triflyl derivatives allo-15a,b with NaN3 or NaOAc in DMF surprisingly afforded allo-9a,b in good yield. © 1988, American Chemical Society. All rights reserved. |
| Keywords: | unclassified drug; nonhuman; methodology; drug synthesis; nuclear magnetic resonance; nicotinamide 5 alpha riboside; nicotinamide 5 beta riboside |
| Journal Title: | Journal of Organic Chemistry |
| Volume: | 53 |
| Issue: | 15 |
| ISSN: | 0022-3263 |
| Publisher: | American Chemical Society |
| Date Published: | 1988-01-01 |
| Start Page: | 3473 |
| End Page: | 3479 |
| Language: | English |
| DOI: | 10.1021/jo00250a013 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 6 August 2020 -- Source: Scopus |
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