Synthesis of ketopyranosyl glycosides and determination of their anomeric configuration on the basis of the three-bond carbon-proton couplings

Gábor Májer, Anikó Borbás, Tünde Zita Illyés, László Szilágyi, Attila Csaba Bényei, András Lipták

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Anomeric pairs of ketopyranosyl glycosides with various substituents at Cα, Cβ and Cγ were synthesized from the corresponding thioglycosides, and the influence of the Cα-Cβ-Cγ-Hγ torsion angle and substituent effects on the three-bond carbon-proton couplings was studied. The cis coupling constants range from 1 to 2 Hz. The trans couplings are generally as small as 2.3-2.6 Hz; however, for compounds bearing an unsubstituted γ-carbon, a relatively large trans coupling was measured (4.8 Hz). An S-ethyl group at the β-position increases the cis coupling (up to 3.2 Hz) compared to the corresponding O-glycosides.

Original languageEnglish
Pages (from-to)1393-1404
Number of pages12
JournalCarbohydrate Research
Volume342
Issue number11
DOIs
Publication statusPublished - Aug 13 2007

Keywords

  • Anomeric configuration
  • Anomeric pairs
  • Glycosylation
  • Karplus relationship
  • Ketopyranosyl glycosides
  • Three-bond carbon-proton coupling constant

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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