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

Abstract

Glycosides of the fully acetylated 3-amino-3,6-dideoxy-L-hexosides in the gluco, galacto, manno, and talo configurations have been treated with chromium trioxide in acetic acid. The α-L-methyl glycosides, which exist in the more stable chair conformation 1C4, with an axially oriented aglycon, are resistant to this oxidation, whereas the β-L-linked glycoside having the gluco configuration (1C4 conformation) and the α-L-methyl glycoside having the talo configuration (4C1 conformation), both with equatorially oriented aglycons, are oxidized to the corresponding 5-adulosonates.