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Glycosylation of triterpene alcohols of the lupane series

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Abstract

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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Additional information

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

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Keywords

  • Alcohol
  • Mercury
  • Organic Chemistry
  • Acetonitrile
  • Cyanide