On the influence of solvent on the stereoselectivity of glycosylation reactions.
Carbohydr Res
; 535: 109010, 2024 Jan.
Article
em En
| MEDLINE
| ID: mdl-38181544
ABSTRACT
Methodology development in carbohydrate chemistry entails the stereoselective formation of C-O bonds as a key step in the synthesis of oligo- and polysaccharides. The anomeric selectivity of a glycosylation reaction is affected by a multitude of parameters, such as the nature of the donor and acceptor, activator/promotor system, temperature and solvent. The influence of different solvents on the stereoselective outcome of glycosylation reactions employing thioglucopyranosides as glycosyl donors with a non-participating protecting group at position 2 has been studied. A large change in selectivity as a function of solvent was observed and a correlation between selectivity and the Kamlet-Taft solvent parameter π* was found. Furthermore, molecular modeling using density functional theory methodology was conducted to decipher the role of the solvent and possible reaction pathways were investigated.
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Base de dados:
MEDLINE
Assunto principal:
Polissacarídeos
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article