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

Carbohydr Res. 2009 May 12;344(7):921-7. doi: 10.1016/j.carres.2009.02.011. Epub 2009 Feb 14.

Abstract

(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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Glycosides