GLYCOSYLATION OF TRITERPENOIDS OF THE DAMMARANE SERIES. IV. β-D-GLUCOPYRANOSIDES OF BETULAFOLIENETRIOL AND ITS DERIVATIVES

Article abstract of DOI:10.1007/BF00598297

The glycosylation of betulafolienetriol (dammar-24-ene-3α,12β,20(S)-triol) under the conditions of the Koenigs-Knorr, the Heflerich, and the orthoester methods has been studied.It has been shown that the condensation of β-folienetriol and its 3-epimer with α-acetobromoglucose in the presence of silver oxide leads to a mixture of the corresponding 3-, 12-, and 20-mono- and 3,12- and 3,20-di-O-β-pD-glucopyranosides.It has been established that the glycosylation of dammar-24-ene-3α,12β,20(S)-triol under Heflerich's conditions and those of the orthoester method is accompanied by a side rea ction of dehydration in the side chain and leads to 20-dehydroxy derivatives.The structures of all the newly obtained compounds have been established on the basis of the results of IR and of 1H and 13C NMR spectroscopy.