1061302-89-3Relevant academic research and scientific papers
Conformational domino effect in saccharides. 2. Anomeric configuration control
Roen, Alfredo,Mayato, Carlos,Padron, Juan I.,Vazquez, Jesus T.
experimental part, p. 7266 - 7279 (2009/05/09)
(Chemical Equation Presented) A series of alkyl β-D-glucopyranosyl- (1→6)-α-D-glucopyranosides were synthesized and analyzed by NMR and CD techniques. As in their β-anomer series, the rotational populations of the hydroxymethyl group involved in the interglycosidic linkage (torsion angle ω) are shown to depend on the aglycon and the solvent. However, for this α-anomer series the rotational dependence arises directly from steric effects. Correlations between rotational populations and molar refractivity (MR) steric parameters, but not Taft's steric parameters (β-anomers), of the alkyl substituents were observed. The conformational domino effect previously predicted from alkyl β-(1→6)-diglucopyranosides is now supported by the conformational properties of their α-anomers, the anomeric configuration controlling the domino effect. In addition, the rotational populations around the C5′-C6′ bond (torsion angle ω′) depend weakly on the structure of the aglycon and the anomeric configuration.
