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Regio- and stereoselective glycosylation of 20(S), 24(R)-epoxydammarane-3,12β,25-triols with cholesteryl (α-D-glucose orthoacetate). III

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Abstract

The glycosylation of 20(S),24(R)-epoxydammarane-3,12β,25-triols under the conditions of the previous formation of an ion pair with a Lewis acid and subsequent treatment with cholesteryl (α-D-glucose orthoacetate) leads to the selective formation with high yields of the corresponding 12-monoglucosides having the trans configuration of the glucosidic bond. The regioselectivity of the direct glycosylation of 20(S), 24(R)-epoxydammarane-3,12β,25-triols by orthoesters is determined by the influence of intramolecular hydrogen bonds in the initial triols. Details of the PMR and13C NMR spectra of the new compounds obtained are given.

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Literature cited

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Authors
  1. N. F. Samoshina
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  2. V. L. Novikov
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  3. V. A. Denisenko
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  4. N. I. Uvarova
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Additional information

Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 315–321, May–June, 1983.

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Samoshina, N.F., Novikov, V.L., Denisenko, V.A. et al. Regio- and stereoselective glycosylation of 20(S), 24(R)-epoxydammarane-3,12β,25-triols with cholesteryl (α-D-glucose orthoacetate). III. Chem Nat Compd 19, 299–304 (1983). https://doi.org/10.1007/BF00579764

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  • DOI: https://doi.org/10.1007/BF00579764

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