REACTION OF SOME 1-DEOXY-2,3-DICARBONYL HEXOSE DERIVATIVES WITH AMINOGUANIDINE (GUANYLHYDRAZINE)

The reaction of 4-O-acetyl-1-deoxy-5,6-O-isopropylidene-2,3-D-erythro and (D-threo)-hexodiulose with aminoguanidine (guanylhydrazine) was investigated at pH 7.0 and 37 degrees C. The two dicarbonyl compounds reacted rapidly to give 6-methyl-5-substituted triazine derivatives, which were fully characterized. The compounds were deblocked in a stepwise manner to give, first the de-O-acetylated compounds and then (by removal of the isopropylidene groups) the free triazine derivatives which were fully characterized (GLC/MS, NMR and elemental analyses).