Synthesis and 13C NMR Spectroscopy of Model Compounds for the Microstructure Analysis of Poly(Vinyl Glycoside)s
A series of glycosylated diol and triol derivatives was synthesized in order to serve as model compounds for the analysis of the stereochemistry, regiochemistry, and defect structures of poly(vinyl glycoside)s. 13C NMR spectroscopic analysis of these compounds revealed that the attached chiral carbohydrate substituents induced a strong correlation of the chemical shifts of both the anomeric C and the α-C atom of the aglycon with the absolute configuration of the latter. The influence of the stereoconfiguration of β- and γ-C atoms as well as the regiochemistry of the aglycon on the chemical shifts of the α-C and the anomeric C atom was also investigated. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)