Conclusions
-
1.
A comparative study was made of the NMR spectra of some 3,6-anhydroglucose and 3,6-anhydrogalactose derivatives, of the free substrates and in the presence of Eu(DPM)3.
-
2.
The assignment of the compounds to the gluco or galacto series can be made on the basis of the values of the chemical shift\(\delta _{{\rm H}^1 } \) of the anomeric proton, the values of the SSCC, and the sequence expressing the gradients of the isotropic shift of the ring protons.
-
3.
The oxygen atom of the 3,6-anhydro unit in the fully substituted derivatives is the center of the predominant coordination with the paramagnetic shifting reagents, and in the case of methyl-2-O-methyl-3,6-anhydro-α-D-galactopyranoside it clearly surpasses the oxygen of the hydroxyl group in its donor capacity.
This is a preview of subscription content, log in via an institution to check access.
Literature cited
A. F. Cockerill, G. L. O. Davies, R. C. Harden, and D. M. Rackham, Chem. Rev.,73, 553 (1973).
A. F. Bochkov, Ya. V. Voznyi, V. M. Kalinevich, A. S. Shashkov, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim.,1975, 415.
R. F. Butterworth, A. G. Pernet, and S. Hanessian, Can. J. Chem.,49, 981 (1971).
S. Farid, A. Ateya, and M. Maggio, Chem. Commun.,1971, 1285.
W. N. Haworth, L. N. Owen, and F. Smith, J. Chem. Soc.1941, 88.
W. N. Haworth, J. Jackson, and F. Smith, J. Chem. Soc.1940, 620.
O. S. Chizhov, B. M. Zolotarev, A. I. Usov, M. A. Rechter, and N. K. Kochetkov, Carbohyd. Res.,16, 29 (1971); K. Izumi, Carbohyd. Res.,27, 278 (1973).
N. S. Anderson, T. C. S. Dolan, and D. A. Rees, J. Chem. Soc. C1968, 596.
S. B. Baker, Can. J. Chem.,32, 628 (1954).
W. N. Haworth, E. L. Hirst, and E. G. Teece, J. Chem. Soc.1931, 2859.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2591–2594, November, 1975.
The authors express their gratitude to Ya. V. Voznyi for supplying the sample of 1,2,4-orthoacetyl-3,6-anhydro-α-D-glucopyranose (VII).
Rights and permissions
About this article
Cite this article
Chizhov, O.S., Shashkov, A.S., Usov, A.I. et al. Use of paramagnetic shifting reagents to study some 3,6-anhydropyranosides. Russ Chem Bull 24, 2478–2480 (1975). https://doi.org/10.1007/BF00921673
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00921673