Dépôt numérique
RECHERCHER

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

Téléchargements

Téléchargements par mois depuis la dernière année

Plus de statistiques...

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.

[thumbnail of Synthesis of Galectin Inhibitors by Regioselective 3'- O-Sulfation of Vanillin Lactosides Obtained under Phase Transfer Catalysis.pdf]
Prévisualisation
PDF - Version publiée
Disponible sous licence Creative Commons Attribution.

Télécharger (1MB) | Prévisualisation

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

Gestion Actions (Identification requise)

Modifier la notice Modifier la notice