Pentafluoropropionyl and trifluoroacetyl groups for temporary hydroxyl group protection in oligomannoside synthesis

Article abstract of DOI:10.1016/S0008-6215(03)00099-5

Pentafluoropropionyl (PFP) and trifluoroacetyl (TFA) esters were demonstrated to be useful in facile oligosaccharide synthesis. These were well compatible with glycosylation conditions and removable by treatment with pyridine-EtOH, with complete preservation of acetyl groups. Analytically pure products were obtained quantitatively, simply by evaporating the reaction mixtures. Using O-PFP and O-TFA carrying glycosyl halides, trisaccharide (Manα1→2Manα1→2Man) and tetrasaccharide (Glcα1→3Manα1→2Manα1→2Man) portions of monoglucosylated high-mannose type dodecasaccharide (Glc₁Man₉GlcNAc₂), a putative ligand for the ER chaperon, calnexin and calreticulin, were synthesized.