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Updated: Sep 26, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Pentafluoropropionyl and trifluoroacetyl groups for temporary hydroxyl group protection in oligomannoside synthesis
Maki Takatani1, Ichiro Matsuo, Yukishige Ito
1RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
Abstract:
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 (Manalpha1-->2Manalpha1-->2Man) and tetrasaccharide (Glcalpha1-->3Manalpha1-->2Manalpha1-->2Man) portions of monoglucosylated high-mannose type dodecasaccharide (Glc(1)Man(9)GlcNAc(2)), a putative ligand for the ER chaperon, calnexin and calreticulin, were synthesized.
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