Facile synthesis of sulfonium ion derivatives of 1,5-anhydro-5-thio-l-fucitol as potential α-l-fucosidase inhibitors

Five sulfonium ion derivatives with 1,5-anhydro-5-thio-l-fucitol as a core structure were efficiently synthesized as potential α-l-fucosidase inhibitors. The key unit, the tri-O-benzyl derivative of l-fucitol, was readily synthesized from methyl α-d-mannopyranoside. Alkylation with methyl iodide or 5-methoxycarbonyl-1-pentyl iodide in acetonitrile containing AgBF4 afforded the corresponding alkylated sulfonium tetrafluoroborates. Alternatively, ring opening of three 1,3-cyclic sulfates in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) containing K2CO3 afforded the corresponding zwitterionic sulfonium sulfates.

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