Chromium trioxide oxidation of acetylated 3-amino-3,6-dideoxy-L-hexosides

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Abstract
Glycosides of the fully acetylated 3-amino-3,6-dideoxy-L-hexosides in the gluco, galacto, manno and talo configurations were treated with chromium trioxide in acetic acid. The .alpha.-L-methyl glycosides, which exist in the more stable chair conformation 1C4, with an axially oriented aglycon, are resistant to this oxidation; however, the .beta.-L-linked glycoside having the gluco configuration (1C4 conformation) and the .alpha.-L-methyl glycoside having the talo configuration (4C1 conformation), both with equatorially oriented aglycons, are oxidized to the corresponding 5-adulosonates. [3-Acetamido-3,6-dideoxy-L-glucose is an integral part of the core oligosaccharide of the lipopolysaccharide of Aeromonas hydrophila.].