Facile synthesis of sulfonium ion derivatives of 1,5-anhydro-5-thio-L-fucitol as potential alpha-L-fucosidase inhibitors |
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Authors: | Gu Guofeng Liu Hui Pinto B Mario |
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Institution: | Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6. |
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Abstract: | 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. |
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Keywords: | l-fucitol" target="_blank">5-Thio-l-fucitol Alkylation Sulfonium tetrafluoroborates Sulfonium sulfates l-fucosidase inhibitors" target="_blank">Potential α-l-fucosidase inhibitors |
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