SYNTHESIS OF 5-AMINO-5-DEOXYPENTONOLACTAMS

-5-deoxy-1,2-O-isopropylidene-alpha-D-xylofuranose (4) and -5-deoxy-1, 2-O-isopropylidene-alpha-D-ribofuranose (10) were prepared starting fr om D-xylose and D-arabinose, respectively. Using the oxidation-reducti on way for the C-3 epimerization, -5-deoxy-1,2-O-isopropylidene-alpha- D-ribofuranose (15) and o-5-deoxy-1,2-O-isopropylidene-beta-D-lyxofura nose (17) were obtained from 4 and 10, respectively. The derivatives 4 , 10, 15 and 17 afforded by acid hydrolysis, oxidation with bromine an d catalytic hydrogenation successively the corresponding 5-azido-5-deo xyD-pentofuranoses 6, 11, 18, 19, 5-azido-5-deoxy-D-pentonolactones 7, 12, 20, 21 and 5-amino-5-deoxy-D-pentonolactams 8, 13, 22, 23.