Abstract
The13C NMR spectra of epimeric C-D-glucopyranosides with alkyl, aryl, and alkynyl substituents have been studied. The diastereomeric effects of the chemical shifts have been determined and assignments have been made to the 1α-and 1β- stereochemical series on the basis of HH COSY and CH HET CORR two-dimensional NMR spectra. The diastereomeric effects observed for the C-3 and C-5 carbon atoms are proposed as characteristic parameters for establishing the stereochemistry at the C-1 carbon atom.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
L. M. Khalilov, E. V. Vasil'ev, O. V. Shitikova, and G. A. Tolstikov, Khim. Prir. Soedin., 363 (1991). [Preceding paper in this issue.]
J. F. Stoddart, Stereochemistry of Carbohydrates, Interscience, New York (1971).
M. A. Sparks and J. S. Panek, Tetrahedron Lett.,30, No. 4, 407–410 (1989).
H. Günther, NMR Spectroscopy, An Introduction, Wiley, New York (1980) [Russian translation from the German, Mir, Moscow (1984)].
W. P. Aue, E. Bartholdi, and R. R. Ernst, J. Chem. Phys.,64, No. 5, 2229–2246 (1976).
A. Bax and G. A. Morris, J. Magn. Res.,42, 501 (1981).
Additional information
Institute of Chemistry, Bashir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 368–373, May–June, 1991.
Rights and permissions
About this article
Cite this article
Khalilov, L.M., Spivak, A.Y., Vasil'eva, E.V. et al. 13C NMR spectra of biologically active compounds XI. Diastereomeric effects in C-glycosides. Chem Nat Compd 27, 318–322 (1991). https://doi.org/10.1007/BF00630317
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00630317