Facile synthesis of sulfonium ion derivatives of 1,5-anhydro-5-thio-L-fucitol as potential alpha-L-fucosidase inhibitors.
Five sulfonium ion derivatives with 1,5-anhydro-5-thio-L-fucitol as a core structure were efficiently synthesized as potential alpha-L-fucosidase inhibitors. The key unit, the tri-O-benzyl derivative of L-fucitol, was readily synthesized from methyl alpha-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.
Gu
Guofeng
G
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6.
Liu
Hui
H
Pinto
B Mario
BM
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000494:pharmacology*; D013452:Sulfonium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D005644:alpha-L-Fucosidase / Q000494:pharmacology*
D004791:Enzyme Inhibitors; D013402:Sugar Alcohols; D013452:Sulfonium Compounds; D005644:alpha-L-Fucosidase