Summary
1. The Koenigs-Knorr condensation of acetobromorhamnose with strophanthidin acetate has given strophanthidin L-rhamnoside substituted at the C5 hydroxyl, and its condensation with free strophanthidin has given strophanthidin di-α-O-rhamnoside substituted at the C3 and C5 hydroxy groups.
2. Under similar conditions, methyl 2,3,4-tri-O-acetyl-l-bromo-1-deoxy-α-D-galacturonate and strophanthidin have given the corresponding strophanthidin diglycoside substituted at the C3 and C5 hydroxyls.
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Literature cited
R. M. Carman, R. G. Coombe, and T. R. Watson, Aust. J. Chem.,17, 573 (1964).
H. Lichti, P. Niklaus, and A. Wartburg, Helv. Chim. Acta,56, 2083, 2088 (1973).
I. F. Makarevich, Khim. Prirodn. Soedin.,191 (1969).
I. F. Makarevich, S. G. Kislichenko, D. G. Kolesnikov, A. Ya. Topchii, and M. A. Angarskaya, Khim. Prirodn. Soedin., 45 (1971).
V. T. Chernobai, Zh. Obshch. Khim.,34, 1690 (1964).
W. W. Zorbach and K. V. Bhat, Adv. Carbohyd. Chem.,22, 273 (1966); K. Takiura, H. Yuki, Y. Okamoto, H. Takai, and S. Honda, Chem. Pharm. Bull.,22, 2263 (1974).
V. T. Chernobai, Zh. Obshch. Khim.,34, 1018 (1964).
K. Reule and T. Reichstein, Helv. Chim. Acta,35, 98 (1952).
R. N. Jones, P. Humphries, F. Herling, and K. Dobriner, J. Am. Chem. Soc.,73, 3215 (1951).
C. Ingold, Structure and Mechanism in Organic Chemistry, second Ed., Cornell Univ. Press, Ithaca, New York (1969).
Ya. V. Rashkes, M. B. Gorovits, G. K. Makarichev, and N. K. Abubakirov, Khim. Prirodn. Soedin., 747 (1971).
Ya. V. Rashkes, Khim. Prirodn. Soedin., 126 (1973).
W. Klyne, Biochem. J.,47, No. 4 xli (1950).
E. Fischer, M. Bergmann, and A. Rabe, Ber.,53, 2362 (1920).
N. K. Kochetkov, Methods of Carbohydrate Chemistry [in Russian], Moscow (1967), p. 124.
S. Morell, L. Baur, and K. P. Link, J. Biol. Chem.,110, 719 (1935).
J. Becker, Biochim. Biophys. Acta,100, 574 (1965).
N. Sh. Pal'yants, A. F. Bochkov, N. K. Abubakirov, Khim. Prirodn. Soedin., 58 (1976).
N. Sh. Pal'yants, M. B. Gorovits, and N. K. Abubakirov, Khim. Prirodn. Soedin., 263 (1975).
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Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 765–772, November–December, 1976.
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Pal'yants, N.S., Gorovits, M.V. & Abubakirov, N.K. Glycosylation of cardenolides. IV. Strophanthidin 5-α-L-rhamnoside and 3,5-bisglycosides. Chem Nat Compd 12, 687–692 (1976). https://doi.org/10.1007/BF00564960
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DOI: https://doi.org/10.1007/BF00564960