Phosphorylated sugars. Part XVI. Synthesis of 3-deoxy-D-glycero-hex-3-en-2-ulofuranos(2,5)onic acid 6-(dihydrogen phosphate)
Abstract
Treatment of glucometasaccharinic acid 6-phosphate with a Sprinson-type vanadium oxide catalyst gives, besides 3-deoxy-D-erythro-hexulosonic acid 6-phosphate, 3-deoxy-D-glycero-hex-3-en-2-ulofuranos-(2,5)onic acid 6-(dihydrogen phosphate). This upon hydrogenation over palladium–carbon, yields, apparently stereospecifically, 3-deoxy-D-erythro-hexulosonic acid 6-phosphate. If [3H]hydrogen is used, 3-deoxy-D-erythro-[3,4-3H2]hexulosonic acid 6-phosphate is obtained.