FURTHER STUDIES OF RUTHENIUM TETROXIDE AS AN OXIDANT FOR CARBOHYDRATE DERIVATIVES

An extension is reported of the evaluation of ruthenium tetroxide as an oxidant for the conversion of partially protected carbohydrates into glycosulose derivatives. It has been demonstrated that free hydroxyl groups in benzoic and toluene-p-sulphonic esters, and in N-acetamido derivatives of glycosides can all be oxidised successfully by the reagent. It has been shown also that the oxidant converts 1,4:3,6-dianhydrohexitols into the corresponding 2,5-dione; no significant selectivity in the oxidation of endo and exo hydroxyl groups was noted. Comment is made on the abnormally high optical rotation of the bis(2,4-dinitrophenylhydrazone) of 1,4:3,6-dianhydro-d-threo-hexo-2,5-diulose. © 1969.