Synthesis of Galectin Inhibitors by Regioselective 3'-O-Sulfation of Vanillin Lactosides Obtained under Phase Transfer Catalysis.
Molecules
; 26(1)2020 Dec 29.
Article
em En
| MEDLINE
| ID: mdl-33383774
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, ß-unsaturated carboxylic acid which was next reduced to the saturated counterpart.
Palavras-chave
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Sulfatos
/
Benzaldeídos
/
Galectinas
/
Glicosídeos
Limite:
Humans
Idioma:
En
Revista:
Molecules
Assunto da revista:
BIOLOGIA
Ano de publicação:
2020
Tipo de documento:
Article
País de afiliação:
Canadá