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

Belkhadem, Karima; Cao, Yihong et Roy, René (2020). Synthesis of Galectin Inhibitors by Regioselective 3'-O-Sulfation of Vanillin Lactosides Obtained under Phase Transfer Catalysis Molecules , vol. 26 , nº e115. pp. 1-12. DOI: 10.3390/molecules26010115.

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Résumé

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.

Type de document:	Article
Mots-clés libres:	Knoevenagel-Doebner Reaction; Cancer; Galectins; Lactosides; Phase Transfer Catalysis; Sulfation; Vanillin
Centre:	Centre INRS-Institut Armand Frappier
Date de dépôt:	23 juin 2022 02:25
Dernière modification:	23 juin 2022 02:25
URI:	https://espace.inrs.ca/id/eprint/12294

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