Collect. Czech. Chem. Commun. 1996, 61, 1027-1036
https://doi.org/10.1135/cccc19961027

Synthesis of 5-Amino-5-deoxypentonolactams

Karel Kefurt, Zdeňka Kefurtová, Věra Marková and Karla Slívová

Department of Natural Compounds, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic

Abstract

5-Azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (4) and 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-arabinofuranose (10) were prepared starting from D-xylose and D-arabinose, respectively. Using the oxidation-reduction way for the C-3 epimerization, 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (15) and 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-lyxofuranose (17) were obtained from 4 and 10, respectively. The derivatives 4, 10, 15 and 17 afforded by acid hydrolysis, oxidation with bromine and catalytic hydrogenation successively the corresponding 5-azido-5-deoxy-D-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.

Keywords: 5-Azido-5-deoxypentoses; 5-Amino-5-deoxypentonolactams; Synthesis.