On the influence of solvent on the stereoselectivity of glycosylation reactions

Carbohydr Res. 2023 Dec 13;535:109010. doi: 10.1016/j.carres.2023.109010. Online ahead of print.ABSTRACTMethodology 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.PMID:38181544 | DOI:10.1016/j.carres.2023.109010
Source: Carbohydrate Research - Category: Genetics & Stem Cells Authors: Source Type: research