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Synthesis and 13 C NMR Spectroscopy of Model Compounds for the Microstructure Analysis of Poly(Vinyl Glycoside)s
Author(s) -
Yuan Jialong,
Frauenrath Holger
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800798
Subject(s) - chemistry , regioselectivity , anomer , chemical shift , stereochemistry , nuclear magnetic resonance spectroscopy , diol , glycoside , carbohydrate chemistry , two dimensional nuclear magnetic resonance spectroscopy , carbon 13 nmr , absolute configuration , organic chemistry , catalysis
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. 13 C 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)