How does the choice of protecting group affect the yield and selectivity in carbohydrate modification reactions?
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The choice of protecting group significantly influences the yield and selectivity in carbohydrate modification reactions. For instance, electron-rich acyl protecting groups, like C4-pivaloylated galactose building blocks, exhibit high α-selectivity, while counterparts with electron-withdrawing groups show lower selectivity. Additionally, the reactivity of acceptor alcohols in glycosylation reactions is heavily dependent on their configuration and substitution pattern, with functional groups flanking the acceptor alcohol playing a crucial role. Furthermore, the introduction of protecting groups to partially protected monosaccharides requires careful consideration of electronic, steric, and conformational effects to ensure optimal reactivity. Overall, the strategic selection of protecting groups is essential for achieving desired outcomes in carbohydrate modification reactions, impacting both yield and selectivity.
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| The choice of protecting group influences yield and selectivity in carbohydrate modification reactions by affecting the reactivity of the acceptor alcohol based on its configuration and substitution pattern. | |
| The choice of protecting group impacts yield and selectivity by influencing reactivity towards acylation. Sterically crowded and conformationally restricted galactosides can exhibit unexpected nucleophile masking, altering reaction pathways. | |
| The choice of protecting group significantly influences yield and selectivity in carbohydrate modification reactions, as demonstrated by substrate-specific closed-loop optimization using Bayesian optimization in the study. | |
| The protecting-group-free glycosylation of phosphatidic acid in aqueous media showed high yield and selectivity, eliminating the need for protecting groups in carbohydrate modification reactions. | |
3 Citations | The electron density in acyl protecting groups influences stereoselectivity in carbohydrate modification reactions. Electron-rich groups enhance α-selectivity, while electron-withdrawing groups reduce it. |
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