Conclusions
-
1.
The13C NMR spectra were obtained and interpreted for aqueous solutions of three parent hexoses: D-talose, D-gulose, and L-idose. The parameters of the PMR spectra for solutions of these compounds in D2O are given.
-
2.
The13C NMR spectra of the L-idose derivatives in aqueous solutions were interpreted for 6-deoxy- and 6-O-methyl-L-idose.
-
3.
The dependence of the13C chemical shifts and\(^1 J_{1_H 1 - 13_C 1} \) spin-spin coupling constants in eight parent hexopyranoses on the position of the conformational equilibrium of the pyranose rings in solutions is discussed.
Similar content being viewed by others
Literature cited
L. D. Hall and L. F. Jonson, Chem. Commun., 509 (1969).
A. S. Perlin and B. Casu, Tetrahedron Lett., (1969) 2921.
A. S. Perlin, B. Casu, and H. J. Koch, Can. J. Chem.,48, 2596 (1970).
P. A. J. Gorin, Can. J. Chem.,52, 458 (1974).
K. Bock and M. B. Sommer, Acta Chem. Scand.,B34, 389 (1980).
W. Voelter and E. Breitmeier, Org. Magn. Reson.,5, 311 (1973).
P. E. Pfeffer, K. M. Valentine, and F. W. Parrish, J. Am. Chem. Soc.,901, 1265 (1979).
J. F. Stoddart, Stereochemistry of Carbohydrates, Wiley-Interscience (1971).
P. E. Hansen, Progr. Nucl. Magn. Reson. Spectrosc.,14, 175 (1981).
A. S. Shashkov and O. S. Chizhov, Bioorg. Khim.,2, 437 (1976).
R. G. S. Ritchie, N. Sir, B. Korsch, J. H. Koch, and A. S. Perlin, Can. J. Chem.,53, 1424 (1975).
H. Paulsen, V. Sinnwell, and W. Greve, Carbohydr. Res.,49, 27 (1976).
P. A. J. Gorin and M. Mazurek, Can. J. Chem.,53, 1212 (1975).
K. Bock, I. Lundt, and C. Pedersen, Tetrahedron Lett., 1037 (1973).
K. Bock and C. Pedersen, J. Chem. Soc. Perkin Trans.2, 293 (1974).
A. S. Meyer and T. Reichstein, Helv. Chim. Acta,29, 152 (1946).
A. S. Meyer and T. Reichstein, Helv. Chim. Acta,29, 139 (1946).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1328–1336, June, 1983.
The author conveys his gratitude to A. F. Sviridov for the synthesis of L-idose and its derivatives.
Rights and permissions
About this article
Cite this article
Shashkov, A.S. 13C NMR spectra of parent hexopyranoses. Russ Chem Bull 32, 1200–1207 (1983). https://doi.org/10.1007/BF00953157
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00953157