Synthesis of some O-, S- and N-glycosides of hept-2-ulopyranosonamides.
(O-Peracylated alpha-D-gluco- and -galacto-hept-2-ulopyranosylbromide)onamides gave the corresponding (alkyl beta-D-glyco-hept-2-ulopyranoside)onamides under Koenigs-Knorr conditions, and similar aryl glycosides were obtained with sodium phenolates; (aryl and hetaryl 2-thio-beta-D-gluco-hept-2-ulopyranoside)onamides were formed with thiophenols in the presence of K(2)CO(3) in acetone, and reactions with aniline in CH(2)Cl(2) furnished (N-phenyl beta-D-glyco-hept-2-ulopyranosylamine)onamides. Some deprotected derivatives of d-gluco configuration obtained by the Zemplén protocol showed no significant inhibition against rabbit muscle glycogen phosphorylase b.
Nagy
Veronika
V
Department of Organic Chemistry (POB 20), University of Debrecen, H-4010 Debrecen, Hungary.
Czifrák
Katalin
K
Bényei
Attila
A
Somsák
László
L
D018360:Crystallography, X-Ray; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D006027:Glycosides