Abstract
The p.m.r. spectra of ethyl 3-(glycosylamino)crotonates derived from d-glucose, d-galactose, d-mannose, and l-rhamnose, and those of their corresponding O-acetyl derivatives, have been examined. The results confirm that the amino and ethoxy-carbonyl groups of the enamine portion of these substances are in cis disposition and intramolecularly bonded. No other isomeric or tautomeric forms could be detected under the conditions used. Pyranose ring sizes and anomeric configurations (gb- l for the rhamnose derivative, and β- d for the remaining compounds) are assigned to the O-acetyl derivatives on the basis of the chemical shifts and coupling constants observed. The same pyranose structures and anomeric configurations are proposed for the parent compounds after considering the chemical shifts and coupling constants of the anomeric protons.
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