J. Kiss, F. Burkhardt
1970
Citations
0
Influential Citations
6
Citations
Journal
Carbohydrate Research
Abstract
Abstract Metabolites of phenetidine and phenacetin, namely, 2-amino-5-ethoxyphenyl β- d -glucopyranosiduronic aicd and 2-acetamido-5-ethoxyphenyl β- d -glucopyranosiduronic acid were synthesized from 5-ethoxy-2-nitrophenol and the d -glucosyluronic bromide, by the method of Koenigs and Knorr. The β anomers of the d -glucopyranosiduronic acid were obtained; these were identical with the natural metabolites. For proof of the anomeric configuration, the corresponding α-anomers of the aryl d -glucosides and d -glucosiduronic acids were also synthesized: condensation of the above aglucon with the Brigl anhydride led to the α- d -glucopyranoside, which was then oxidized to the corresponding α- d -glucopyranosiduronic acid. The o.r.d. and c.d. spectra of these aryl α- and β- d -glucopyranosides and - d -glucopyranosiduronic acids were recorded, and preliminary indications as to a relationship between the sign of the Cotton effect in the region of 274–280 nm and the anomeric configuration were obtained. Furthermore, some data from the n.m.r. spectra of the pure anomers of these d -glucosides and d -glucopyranosiduronic acids are given.