Synthesis of Galectin Inhibitors by Regioselective 3′-O-Sulfation of Vanillin Lactosides Obtained under Phase Transfer Catalysis |
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Authors: | Karima Belkhadem Yihong Cao Ren Roy |
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Institution: | 1.Department of Chemistry, University of Québec à Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, QC H3C 3P8, Canada; (K.B.); (Y.C.);2.INRS-Institut Armand-Frappier, Université du Québec, 531 boul. des Prairies, Laval, QC H7V 1B7, Canada |
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Abstract: | Vanillin-based lactoside derivatives were synthetized using phase-transfer catalyzed reactions from per-O-acetylated lactosyl bromide. The aldehyde group of the vanillin moiety was then modified to generate a series of related analogs having variable functionalities in the para- position of the aromatic residue. The corresponding unprotected lactosides, obtained by Zemplén transesterification, were regioselectively 3′-O-sulfated using tin chemistry activation followed by treatment with sulfur trioxide-trimethylamine complex (Men3N-SO3). Additional derivatives were also prepared from the vanillin’s aldehyde using a Knoevenagel reaction to provide extended α, β-unsaturated carboxylic acid which was next reduced to the saturated counterpart. |
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Keywords: | lactosides galectins vanillin cancer sulfation phase transfer catalysis Knoevenagel-Doebner reaction |
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