Preparation of 2,6-anhydro-aldose acylhydrazones, -semicarbazones and -oximes from 2,6-anhydro-aldononitriles (glycosyl cyanides).
Reductive transformation of per-O-acylated 2,6-anhydro-aldononitriles (glycopyranosyl cyanides of the D-galacto, D-gluco, D-xylo, and D-arabino configuration) with Raney-nickel-NaH(2)PO(2) in pyridine-AcOH-water solvent mixture in the presence of benzoylhydrazine, ethyl carbazate, and semicarbazide gave the corresponding anhydro-aldose benzoylhydrazones, -ethoxycarbonylhydrazones, and -semicarbazones, respectively. Acid catalyzed transimination of the semicarbazones with thiosemicarbazide, hydroxylamine, and O-benzylhydroxylamine, resulted in the formation of anhydro-aldose thiosemicarbazones, and E/Z mixtures of anhydro-aldose oximes, and O-benzyl-(anhydro-aldose)-oximes, respectively.
Tóth
Marietta
M
Department of Organic Chemistry, University of Debrecen, H-4010, P.O. Box 20, Debrecen, Hungary.
Somsák
László
L
D000143:Acids / Q000737:chemistry; D001391:Azo Compounds / Q000138:chemical synthesis; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis; D006031:Glycosylation; D006835:Hydrazones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D012664:Semicarbazones / Q000138:chemical synthesis* / Q000737:chemistry
D000143:Acids; D001391:Azo Compounds; D006027:Glycosides; D006835:Hydrazones; D009570:Nitriles; D010091:Oximes; D012664:Semicarbazones