Heterocyclic derivatives of sugars: the formation of 1-glycosyl-3-methylpyrazol-5-ones from hydrazones.
Conditions to effect the conversion of monosaccharide and disaccharide hydrazones to 1-glycosyl-3-methylpyrazol-5-ones were examined. The sugar pyrazolone derivatives were sensitive to oxidation, but high yields were achieved with 2,2,2-trifluoroethyl acetoacetate in mildly acidic solution. Azo coupling of the pyrazolones produced highly coloured azopyrazolone derivatives that prevented further degradation, and these may prove useful labels for chromatographic analysis of carbohydrates.
Kett
W C
WC
Department of Chemistry, Macquarie University, NSW, Australia. wkett@waimr.uwa.edu.au
Batley
M
M
Redmond
J W
JW
D000090:Acetoacetates / Q000737:chemistry; D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D004396:Coloring Agents / Q000138:chemical synthesis / Q000737:chemistry; D004187:Disaccharides / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry; D015335:Molecular Probes / Q000138:chemical synthesis; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000090:Acetoacetates; D001391:Azo Compounds; D004396:Coloring Agents; D004187:Disaccharides; D006027:Glycosides; D006571:Heterocyclic Compounds; D006835:Hydrazones; D015335:Molecular Probes; D009005:Monosaccharides; D011720:Pyrazoles; C024840:ethyl acetoacetate