Preparation of α- and β-dienyl glycosides used as dienes in aqueous Diels-Alder reactions. Influence of the carbohydrate moiety on the thermodynamics of the reaction

A series of 1,3-butadienyl glycosides (mono- and di-saccharides) have been prepared and the kinetics of their Diels-Alder reaction with buten-2-one in water have been studied. The activation parameters for these aqueous cycloadditions provide clues for the hydration structure of such glyco-organic compounds.