sapogenins and triethylamine

Chemical synthesis of two trisaccharides related to the triterpenoid saponins isolated from Solanum lycocarpum from commercially available D-Glc, D-Gal and L-Rha have been achieved by following concise and high-yielding route. The target trisaccharide 1 has been made by following a bis-glycosylation approach that has minimized the protecting group manipulations up to great extent. The trisaccharides have been synthesized in the form of their p-methoxyphenyl (OMP) glycosides to leave the scope for further glycoconjugates formation by the selective removal of the OMP glycoside and trichloroacetimidate chemistry. La(OTf)(3) has been used successfully as the promoter for the NIS mediated activation of thioglycosides.

Topics: Catalysis; Ethylamines; Glycosylation; Hydrogenation; Plant Extracts; Sapogenins; Saponins; Solanum; Triterpenes