
TY  - JOUR
A1  - Angyal, SJ 
A1  - James, K 
T1  - Oxidation of carbohydrates with chromium trioxide in acetic acid. I. Glycosides
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1970
VL  - 23
IS  - 6
SP  - 1209
EP  - 1221
KW  - 
UR  - https://doi.org/10.1071/CH9701209 
N2  - 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. 
ER  -

