
%0 Journal Article
%A Anet, EFLJ 
%T Degradation of carbohydrates IV. Formation of <I>cis</I>-unsaturated hexosones
%J Australian Journal of Chemistry
%D 1963/04/01
%V 16
%N 2
%P 270-277
%K 
%R https://doi.org/10.1071/CH9630270
%U https://www.publish.csiro.au/paper/CH9630270 
%X Two stereospecific methods are described for the formation of the cis-isomer of unsaturated D-hexosone, 1,5-epoxy-l&#945;&#946;,6-dihydroxy-D-glycero-hex-cis-3-en-2-one (X). One method is to heat 3-deoxy-D-erythro-hexosone with dilute acid, and the other to treat 2,3-di-0-methyl-D-glucose first with calcium hydroxide then with acid. The 6-methyl ether of (X) is formed from 2,3,6-tri-O-methyl-D-glucose and from 2,3,4,6-tetra-O-methyl-D-glucose by the calcium hydroxide treatment method. The unsaturated osones are probably formed from an intermediate, the enolic form of a 3-deoxyosone, by an acid-catalysed oxotropic rearrangement. 
