Conclusions
Two methods for the synthesis of C-methyldesoxy-sugars were proposed by desoxygenation of tertiary alcohol xanthogenates and hydrozirconation of exomethylene derivatives of carbohydrates.
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Literature cited
N. K. Kochetkov, A. F. Sviridov, M. S. Ermolenko, D. V. Yashunskii, and O. S. Chizkov, Carbohydrates in Synthesis of Natural Compounds [in Russian], Nauka, Moscow (1984).
S. Hanessian, Total Synthesis of Natural Products: the Chiron Approach, Pergamon Press, Oxford (1983).
W. Hartwig, Tetrahedron,39, 2609 (1983).
D. H. R. Barton and S. W. McCombie, J. Chem. Soc. Perkin Trans., 1, 1574 (1975).
L. Coftier, G. Mabilon, and G. Descotes, J. Heterocycl. Chem.,20, 963 (1983).
A. F. Sviridov, M. S. Ermolenko, D. V. Yashunsky, A. S. Shashkov, and N. K. Kochetkov, Carbohydr. Res.,136, 101 (1985).
J. S. Brimacombe, Angew. Chem.,81, 415 (1969).
J. S. Brimacombe, A. J. Rollins, and S. W. Thompson, Carbohydr. Res.,31, 108 (1973).
G. Just and C. Luthe, Can. J. Chem.,58, 1799 (1980).
N. K. Kochetkov, A. F. Sviridov, and M. S. Ermolenko, Tetrahedron Lett.,22, 4319 (1981).
A. F. Sviridov, M. S. Ermolenko, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim., 2561 (1982).
A. F. Sviridov, D. V. Yashunskii, M. S. Ermolenko, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim., 723 (1984).
A. F. Sviridov, A. Ya. Shmyrina, O. S. Chizhov, and N. K. Kochetkov, Bioorg. Khim.,6, 1647 (1980).
J. Patroni and R. V. Stick, J. Chem. Soc. Chem. Communs, 449 (1978).
J. J. Patroni and R. V. Stick, Austral. J. Chem.,32, 411 (1979).
T. S. Fuiller and R. V. Stick, Austral. J. Chem.,33, 2509 (1980).
J. R. Rasmussen, C. J. Slinger, R. J. Kordish, and D. D. Newman-Evans, J. Org. Chem.,46, 4843 (1981).
H. Redlich, H.-J. Newmann, and H. Paulsen, Chem. Ber.,110, 2911 (1977).
K. S. Chen and J. K. Kochi, J. Am. Chem. Soc.,96, 1383 (1974).
D. H. R. Barton, W. Hartwig, and W. B. Motherwell, J. Chem. Soc. Chem. Communs, 447 (1982).
F. Baumberger and A. Vasella, Helv. Chim. Acta,66, 2210 (1983).
D. W. Hart and J. Schwartz, J. Am. Chem. Soc.,96, 8115 (1974).
A. Rosenthal and M. Sprinzl, Can. J. Chem.,47, 3941 (1969).
B. Weidmann and D. Seebach, Angew. Chem. Inst. Ed. Engl.,22, 31 (1983).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No, 2, pp. 441–445, February, 1986.
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Kochetkov, N.K., Sviridov, A.F., Yashunskii, D.V. et al. Synthesis of C-methyldesoxy sugars: Desoxygenation of tertiary alcohol xanthogenates and hydrozirconation of exomethylene derivatives of carbohydrates. Russ Chem Bull 35, 408–413 (1986). https://doi.org/10.1007/BF00952937
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DOI: https://doi.org/10.1007/BF00952937