Phosphorylated sugars. Part XV. Syntheses of 3-deoxy-D-erythro- and 3-deoxy-D-threo-hexulosonic acid 6-(dihydrogen phosphates)

Abstract

The title compounds were obtained by oxidation of glucometasaccharinic acid and 3-deoxy-D-xylo-hexonic acid 6-phosphates with vanadium(V) oxide–potassium chlorate and isolated by ion-exchange chromatography. Although fairly stable in N-hydrochloric acid at 50°, 3-deoxy-D-erythro-hexulosonic acid 6-phosphate is rapidly destroyed by 0·1N-hydrochloric acid at 95°. When treated with bases of various strengths the same compound undergoes aldol cleavage between C-3 and -4 and gives pyruvic acid and D-glyceraldehyde phosphate; the latter is immediately transformed into DL-lactic acid and phosphate ion. Concomitant with this reaction, alkali-stable phosphate esters of unknown structure are also formed.