Chromium trioxide oxidation of acetylated 3-amino-3,6-dideoxy-L-hexosides.
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 alpha-L-methyl glycosides, which exist in the more stable chair conformation 1C4, with an axially oriented aglycon, are resistant to this oxidation, whereas 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.
D000107:Acetylation; D000333:Aeromonas; D002236:Carbohydrate Conformation; D002857:Chromium; D017608:Chromium Compounds; D006027:Glycosides; D010084:Oxidation-Reduction
D017608:Chromium Compounds; D006027:Glycosides; D002857:Chromium; C028801:chromium trioxide