637316-89-3Relevant academic research and scientific papers
Regioselective esterification of various D-glucopyranosides: Synthesis of a fully protected disaccharide unit of hyaluronic acid
Lu, Xin-An,Chou, Chien-Hung,Wang, Cheng-Chung,Hung, Shang-Cheng
, p. 1364 - 1366 (2003)
A highly regioselective esterification of various D-glucopyranosides with triethylamine and acid anhydrides in excellent yields is described here. Its application toward the synthesis of a fully protected disaccharide unit of hyaluronic acid is also highlighted.
Conformational domino effect in saccharides. 2. Anomeric configuration control
Roen, Alfredo,Mayato, Carlos,Padron, Juan I.,Vazquez, Jesus T.
scheme or table, 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.
