Concise Synthesis of a Pentasaccharide Related to the Anti-Leishmanial Triterpenoid Saponin Isolated from Maesa balansae

Concise synthesis of the glycone part (a pentasaccharide) of the anti-leishmanial triterpenoid saponin isolated from Maesa balansae is reported. A late-stage TEMPO-mediated oxidation of a primary hydroxyl group to carboxylic acid has been achieved under phase-transfer conditions. Glycosylations were performed either by thioglycoside or glycosyl trichloroacetimidate activation using sulfuric acid immobilized on silica (H₂SO₄−silica) in conjunction with N-iodosuccinimide and alone, respectively. H₂SO₄−silica was proved to be a better choice as promoter than conventional Lewis acid promoters such as TfOH or TMSOTf.