The focus of this work is the synthesis of bidesmosidic saponin mimetics. Therefore, dihydrodiosgenin derivs., which differ from the natural compds. by redn. of the 22-(hemi) acetal were used as glycosyl acceptors. In preliminary studies, the dihydrodiosgenin glycosides, as well as trisaccharide, were synthesized. The acceptors were subjected to DMTST-mediated glucosylation for the synthesis of the chacotriose-substituted compd. For a selective 2,4-di-rhamnosylation of the dihydrodiosgenin glucopyranoside, differentiation of the glucose OH groups was achieved by selective benzoylation with 1-(benzoyloxy)benzotriazole. Reaction of the 3,6-di-O-benzoate with the perbenzoylated Et thiorhamnopyranoside donor gave the 2,4-di-rhamnosylated compd., together with the mono-rhamnosylated deriv. [on SciFinder (R)]