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

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Abstract

(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.

Original languageEnglish
Pages (from-to)921-927
Number of pages7
JournalCarbohydrate Research
Volume344
Issue number7
DOIs
Publication statusPublished - máj. 12 2009

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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