Perfluoroalkylation of Nitrones for the Synthesis of a Series of Fucosidase Inhibitors.

摘要: Fucosidase inhibitors represent captivating targets for various biological applications. Iminosugars featuring a fluoroalkyl chain in the pseudoanomeric position were synthesized by nucleophilic addition of perfluoroalkyl Grignard reagent to nitrone. Reduction N–O bond hydroxylamine was achieved treatment with an aqueous solution sulfur dioxide. The pKa = 4.5 target pyrrolidine reflected strong electronic effect chain. Inhibitory potencies fluorinated iminosugars and their corresponding hydroxylamines evaluated against α-L-fucosidase at pH values.