J. Hirsch et al., REACTION OF SOME 1-DEOXY-2,3-DICARBONYL HEXOSE DERIVATIVES WITH AMINOGUANIDINE (GUANYLHYDRAZINE), Journal of carbohydrate chemistry, 14(8), 1995, pp. 1179-1186
The reaction of -acetyl-1-deoxy-5,6-O-isopropylidene-2,3-D-erythro and
(D-threo)-hexodiulose with aminoguanidine (guanylhydrazine) was inves
tigated at pH 7.0 and 37 degrees C. The two dicarbonyl compounds react
ed rapidly to give 6-methyl-5-substituted triazine derivatives, which
were fully characterized. The compounds were deblocked in a stepwise m
anner to give, first the de-O-acetylated compounds and then (by remova
l of the isopropylidene groups) the free triazine derivatives which we
re fully characterized (GLC/MS, NMR and elemental analyses).