
%0 Journal Article
%A Angyal, SJ 
%A Evans, ME 
%T Oxidation of carbohydrates with chromium trioxide in acetic acid. III. Synthesis of the 3-hexuloses
%J Australian Journal of Chemistry
%D 1972/07/01
%V 25
%N 7
%P 1495-1512
%K 
%R https://doi.org/10.1071/CH9721495
%U https://www.publish.csiro.au/paper/CH9721495 
%X The D-arabino, L-lyxo, and L-xylo isomers of 3-hexulose have been synthesized by oxidation, with chromium trioxide in acetic acid, of fully acetylated derivatives of 3,4-0-ethylidene-D-mannitol, 3,4-0-ethylidene-L-iditol, and 2,4-O-benzylidene-D-glucitol, respectively. The D-ribo isomer has been obtained from the L-lyxo compound by inversion at C5. The 3-hexuloses were characterized as their crystalline di-O-isopropylidene derivatives: the arabino- and ribo-hexuloses each give three diacetals. The stereochemistry of these derivatives, and of the spiro-acetals of ketoses in general, is discussed. 
