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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 (Men 3 N-SO 3 ). 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.

Synthesis of Galectin Inhibitors by Regioselective 3′-O-Sulfation of Vanillin Lactosides Obtained under Phase Transfer Catalysis