PMID: 11312934Apr 21, 2001Paper

An examination of the purported reverse anomeric effect beyond acetylated N-xylosyl- and N-glucosylimidazoles

The Journal of Organic Chemistry
A R Vaino, W A Szarek

Abstract

Syntheses of six new N-(pentopyranosyl)imidazoles have been achieved, and their conformations were observed with and without protonation. A decisive decrease in J(5',4), consistent with stabilization of the 1C4 conformations, was clearly observed for three N-(pentopyranosyl)imidazoles. As well, no reverse anomeric stabilization was observed for N-(2,3,4-tri-O-acetyl-alpha-D-lyxopyranosyl)imidazole upon protonation. It is suggested that the previous observations of the reverse anomeric effect were due to the slight increase in steric bulk of the imidazole aglycone upon protonation, along with favorable dipolar interactions between ring substituents, and not by a reverse of the anomeric effect.

Citations

Nov 19, 2015·Carbohydrate Research·Karin ThorsheimUlf Ellervik
Jul 29, 2006·The Journal of Organic Chemistry·Hans GrundbergUlf Ellervik
Apr 27, 2002·The Journal of Organic Chemistry·Tamotsu SuzukiNoritaka Chida

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