Synthesis of a Lividomycin B Analogue, 5-O-[3-O-(2-Amino-2-deoxy-a-d-grlucopyranosyl)-ß-d-ribofuranosyl]-3'-deoxyparomamine

5-O-[3-O-(2-Amino-2-deoxy-a-d-glucopyranosyl)-ß-d-ribofuranosyl]-3'-deoxyparomamine was prepared by two different routes. The first route involves glycosylation of a protected N: 6-O-carbonyl-3'-deoxyparomamine with a protected 3-O-(2-amino-2-deoxy-a-d-glucopyranosyl)ribofuranosyl bromide and subsequent removal of the protecting groups. In the second route, 1-N: 6-O-carbnyl-3'-deoxyparomamine was glycosylated with a protected ribosyl bromide having 3-O-benzylthiocarbonyl group to give a pseudotrisaccharide and, after de-3-O-benzylthiocarbonylation, the product was further condensed with a protected 1-bromide of 2-amino-2-deoxy-d-glucose. This synthesized lividomycin B analogue showed only very weak antibacterial activity and the role of the 6'?-amino group of lividomycin in the action was suggested.