The carbohydrate subunits carrying an N-O-interglycosidic bond play a very important role in the biological activity of the enediyne antibiotics. Condensation of O-(α- and β-D-glucopyranosyl)hydroxylamine (5a and 5b) with the hex-3-ulopyranoside (6) furnished methyl 4,6-O-benzylidene-2,3-dideoxy-3-(2,3,4,6-tetra-O-benzyl-α-D- glucopyranosyloxy)imino-α- and β-D-erythro-hexopyranoside (7a and 7b). Stereoselective reduction of the C=N bond of 7a and 7b with sodium cyanoborohydride resulted in the formation of the required protected N-O-interglycosidic disaccharides (8a and 8b). Finally, catalytic hydrogenation of 8a afforded methyl 2,3-dideoxy-3-(α-D-glucopyranosyloxy)amino-α-D-ribo- hexopyranoside (9a). Under similar conditions the β anomer 8b underwent decomposition.
- H and C NMR
- N-O-interglycosidic disaccharide
ASJC Scopus subject areas
- Analytical Chemistry
- Organic Chemistry