Glucosides have been synthesized from dammar-24-ene-3α,12β,17α,20(S)-tetraol (betulafolienetetraol), isolated from the leaves ofBetula pendula. Condensation with α-acetobromoglucose in the presence of silver oxide and silicate has given acetylated betulafolienetetraol 3- and 12- mono- and 3,12- and 3,20-di-O-β-D-glucopyranosides, the total yield of which amounted to 75–80%. The structures of the semisynthetic glycosides have been established on the basis of the results of IR,1H and13C NMR spectroscopy.
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Atopkina, L.N., Samoshina, N.F., Denisenko, V.A. et al. Glycosylation of triterpenoids of the dammarane series. VII. Dammar-24-ene-3α,12β,17α,20(S)-tetraol β-D-glucopyranosides. Chem Nat Compd 24, 190–193 (1988). https://doi.org/10.1007/BF00596748
- Organic Chemistry
- Total Yield