Synthesis of galactofuranosyl-containing oligosaccharides corresponding to the glycosylinositolphospholipid of Trypanosoma cruzi Original Research Article

The oligosaccharide β-d-Galf-(1→3)-α-d-Manp-(1→2)-[β-d-Galf-(1→3)]-α-d-Manp-(1→2)-α-d-Manp corresponds to the terminal end of the glycosylinositolphospholipid oligosaccharide of the protozoan Trypanosoma cruzi, the causative agent of Chagas’ disease. Syntheses of methyl or ethylthio glycosides of the terminal disaccharide, trisaccharide, tetrasaccharide, and pentasaccharide corresponding to this structure are described. These syntheses employ the selective activation of a phenyl 1-selenogalactofuranoside or a phenyl 1-selenomannopyranoside donor over ethyl 1-thioglycoside acceptors with NIS–TfOH.