Synthesis of some O-, S- and N-glycosides of hept-2-ulopyranosonamides

(O-Peracylated α-d-gluco- and -galacto-hept-2-ulopyranosylbromide)onamides gave the corresponding (alkyl β-d-glyco-hept-2-ulopyranoside)onamides under Koenigs–Knorr conditions, and similar aryl glycosides were obtained with sodium phenolates; (aryl and hetaryl 2-thio-β-d-gluco-hept-2-ulopyranoside)onamides were formed with thiophenols in the presence of K2CO3 in acetone, and reactions with aniline in CH2Cl2 furnished (N-phenyl β-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.