CARBOHYDRATES CONTAINING NITROGEN IN A FIVE-MEMBERED RING AND AN ATTEMPTED SYNTHESIS OF A CARBOHYDRATE WITH NITROGEN IN A SEVEN-MEMBERED RING

Abstract

Lead tetraacetate oxidation of 6-acetamido-6-deoxy-D-galactose (IX) yielded a syrup which was converted to a compound formulated as 4-acetamido-4-deoxy-1,2-O-isopropylidene-D-threofuranose (XII). The same syrup was obtained by alkaline degradation of the product of oxidation of 5-acetamido-5-deoxy-D-xylose diethyl dithioacetal (XVII) with peroxypropionic acid. Treatment of compound XII with p-toluenesulfonyl chloride yielded crystalline 4-acetamido-4-deoxy-1,2-O-isopropylidene-3-O-p-tolylsufonyl-D-threofuranose (XIII).Demercaptalation of 6-acetamido-2,3,4,5-tetra-O-acetyl-6-deoxy-D-galactose diethyl dithioacetal (XX) with mercuric chloride and cadmium carbonate in aqueous acetone did not yield a nitrogen-containing septanose ring but an acyclic derivative.