CATALYTIC REARRANGEMENT OF A 20(S),24(R)-EPOXYDAMMARANE-3β,12α,25-TRIOL (α-D-GLUCOSE 1,2-ORTHOACETATE). II.

Article abstract of DOI:10.1007/BF00580552

The catalytic rearrangement of 20(S),24(R)-epoxydammarane-3β,12α,25-triol 3,12-di(β-D-glucose orthoacetate) leads to the formation of a complex mixture of products, predominating among which are the corresponding 12-monoglucoside and 20(S),24(R)-epoxydammar-12-ene-3β,25-diol.As compared with the rearrangement of the 20(S),24(R)-epoxydammarane-3β,12β,25-triol 3,12-diorthoester the rearrangement of the 20(S),24(R)-epoxydammarane-3β,12α,25-triol 3,12-diorthoester takes place less regioselectively, which is apparently due to the strength of an intramolecular hydrogen bond.The results of IR, PMR, and 13C NMR spectroscopy for the compo unds newly obtained are given.