| 1. |
- Dorst, Kevin M., et al.
(author)
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On the Influence of Solvent on the Stereoselectivity of Glycosylation Reactions
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Other publication (other academic/artistic)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 aglycosylation reaction is affected by a multitude of parameters, such as the nature of the donor andacceptor, activator/promotor system, temperature and solvent. The influence of different solvents onthe stereoselective outcome of glycosylation reactions employing thioglucopyranosides as glycosyldonors with a non-participating protecting group at position 2 has been studied. A large change inselectivity 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 functionaltheory methodology was conducted to decipher the role of the solvent and possible reaction pathwayswere investigated.
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| 2. |
- Dorst, Kevin, 1992-, et al.
(author)
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On the influence of solvent on the stereoselectivity of glycosylation reactions
- 2024
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In: Carbohydrate Research. - 0008-6215 .- 1873-426X. ; 535
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Journal article (peer-reviewed)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 pi* 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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