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: Article

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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