
%0 Journal Article
%A James, K 
%A Angyal, SJ 
%T New synthesis of 1-deoxyhexuloses
%J Australian Journal of Chemistry
%D 1972/09/01
%V 25
%N 9
%P 1967-1977
%K 
%R https://doi.org/10.1071/CH9721967
%U https://www.publish.csiro.au/paper/CH9721967 
%X By displacement of a nitrobenzene-p-sulphonyloxy group by iodide ion from position 1 of 2,3:4,6-di-O-isopropylidene-&#945;-L-sorbofuranose and 2,3:4,5-di-O-iso-propylidene-&#946;-D-fructopyranose, and subsequent hydrogenolysis, 1-deoxy-L-sorbose and 1-deoxy-D-fructose, respectively, have been synthesized. Inversion by oxidation with ruthenium tetroxide, and subsequent reduction, provided new syntheses of D-tagatose and 1-deoxy-L-psicose. The N.M.R. spectrum shows that the aqueous solution of 1-deoxy-D-fructose contains a considerable proportion of the keto form; this proportion increases with increasing temperature. 
