
%0 Journal Article
%A Angyal, SJ 
%A James, K 
%T Oxidation of carbohydrates with chromium trioxide in acetic acid. I. Glycosides
%J Australian Journal of Chemistry
%D 1970/06/01
%V 23
%N 6
%P 1209-1221
%K 
%R https://doi.org/10.1071/CH9701209
%U https://www.publish.csiro.au/paper/CH9701209 
%X Fully acetylated methyl &#946;-D-hexopyranosides are oxidized by chromium trioxide in acetic acid to acetylated methyl 5-hexulosonates. Catalytic hydrogenation of these keto esters leads into the L-series. The corresponding a-D-glycosides are not oxidized in the same way, with the exception of methyl tetra-O-acetyl-&#945;-D-idopyranoside. Both &#945;- and &#946;-anomers of the acetylated fnranosides are oxidized to   aoetylated methyl 4-hexulosonates. The octaacetates of &#945;- and &#946;-lactose are similarly oxidized, the ring of the galactose moiety being opened. The methyl pyranoside of a branched-chain sugar, with no hydrogen atom on C5, is oxidized to a 4-keto ester, acetyl migration occurring from O4 to O5. 
