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

doi:10.1016/j.carres.2007.05.006

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

Carbohydr Res. 2007 Aug 13;342(11):1393-404. doi: 10.1016/j.carres.2007.05.006. Epub 2007 May 18.

Authors

Gábor Májer¹, Anikó Borbás, Tünde Zita Illyés, László Szilágyi, Attila Csaba Bényei, András Lipták

Affiliation

¹ Research Group for Carbohydrates of the Hungarian Academy of Sciences, PO Box 94, Debrecen H-4010, Hungary.

PMID: 17553473
DOI: 10.1016/j.carres.2007.05.006

Abstract

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

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Carbon / chemistry*
Disaccharides / chemical synthesis
Glycosides / chemical synthesis*
Glycosides / chemistry
Protons*
Stereoisomerism
Thioglycosides / chemical synthesis

Substances

Disaccharides
Glycosides
Protons
Thioglycosides
Carbon