Preparation of alpha -and beta-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.
Lubineau
A
A
Laboratoire de Chimie Organique Multifonctionnelle, Institut de Chimie Moléculaire d'Orsay, Université Paris-Sud, France.
Bienaymé
H
H
Queneau
Y
Y
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013816:Thermodynamics
D004187:Disaccharides; D006027:Glycosides