C-nucleosides. Part 1. Preparation of tiazofurin and N-substituted tiazofurins from benzyl (2′,3′,5′-tri-O-benzoyl-β-D-ribofuranosyl)penicillinate
Abstract
The title penicillinate (11 a)—assembled from 2,5-anhydro-3,4,6-tri-O-benzoyl-D-allonic acid (12e) and benzyl 6β-aminopenicillanate (13a)—has been transformed into tiazofurin (6a), N-[(1R)-1-carbamoyl-2-methylprop-2-enyl]tiazofurin (6c), and N-(1-methoxycarbonyl-2-methylprop-1- enyl)-tiazofurin (6d).