Investigation of glycosylating properties of 1-deoxy-1-ethoxysulfonyl-hept- 2-ulopyranosyl derivatives. Synthesis of a new sulfonic acid mimetic of the sialyl Lewis X tetrasaccharide

Magdolna Csávás, Gábor Májer, Mihály Herczeg, Judit Remenyik, László Lázár, Attila Mándi, Anikó Borbás, Sándor Antus

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Glycosylation reactions of the ethylthio, bromo and chloro derivatives of 1-deoxy-1-ethoxysulfonyl-hept-2-ulopyranose were studied applying different acceptors under different conditions. Elimination side-reactions affording exo- and endoglycals occured in all cases, however, with different proportions. Glycosyl chloride donor was applied to glycosylate a trisaccharide acceptor obtaining a new sulfonic acid mimetic of the sialyl Lewis X tetrasaccharide in high yield.

Original languageEnglish
Pages (from-to)1527-1533
Number of pages7
JournalCarbohydrate Research
Volume346
Issue number12
DOIs
Publication statusPublished - Sep 6 2011

Keywords

  • Carbohydrate sulfonic acid
  • Elimination
  • Glycosylation
  • Ketopyranosyl glycosides
  • Sialyl Lewis X mimetic

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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