The glycosylation of lupeol, allobetulin, 3β-28-dihydroxy-18-lupene, 3β-28-dihydroxy-18β, 19β-epoxylupane and of betulin monoacetates in acetonitrile with mercury cyanide has been studied. The 3- and 28-mono- and the 3,28-di-O-β-D-glucopyranosides of 3β-28-dihydroxy-18-lupene and of 3β-28-dihydroxy-18β, 19β-epoxylupane have been synthesized for the first time. Preparative methods for the synthesis of glucosides of lupeol, of allobetulin, and of betulin 3- and 28-monoacetates are proposed.
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L. É. Odinokova, G. I. Oshitok, V. A. Denisenko, V. F. Anufriev, A. M. Tolkach and N. I. Uvarova, Khim. Prir. Soedin, 182 (1984).
A. V. Nikolaev, A. S. Shashkov, B. A. Dmitriev, and N. K. Kochetkov, Bioorg. Khim.7, No. 6, 914 (1981).
J. L. Simonsen and W. C. J. Ross, The Terpenes, Cambridge University Press, Cambridge, Vol. 4 (1957), p. 304.
L. Ruzicka, A. H. Lamberton and E. W. Christe, Helv. Chim. Acta,21, 1706–1717 (1938).
A. Vystrcil, E. Stejskolova-Vondraskova and J. Cerny, Czech. Chem. Commun.,24, No. 10, 3279 (1959).
H. W. Kircher, Phytochemistry,19, No. 12, 2707 (1980).
E. Suokas and T. Hase, Acta Chem. Scand.,B29, No. 1, 139 (1975).
E. Suokas and T. Hase, Acta Chem. Scand.,B28, No. 7, 793 (1974).
E. Suokas and T. Hase, Acta Chem. Scand.,B31, No. 3, 231 (1977).
Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 212–217, March–April, 1988.
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Odinokova, L.É., Denisenko, M.V., Denisenko, V.A. et al. Glycosylation of triterpene alcohols of the lupane series. Chem Nat Compd 24, 178–183 (1988). https://doi.org/10.1007/BF00596745
- Organic Chemistry