| dc.description.abstract | In the realm of glycoscience, the synthesis of polysaccharides stands as a critical endeavor, necessitating the attainment of high purity, optimal yield, and precise stereoselectivity. While the construction protocols of 1,2-trans linkages rely on neighboring group effect, there is no straightforward solution for the formation of 1,2-cis glycosidic bonds.
Recent investigations have underscored the strategic introduction of C-3, C-4, C-6 ester groups on various glycosyl donors as a way to facilitate the formation of 1,2-cis glycosidic linkages, attributed to the remote participation. However, the elucidation of the mechanism and impact of the remote participation remains enigmatic, prompting dispute within the scientific community. Employing an array of analytical techniques including NMR (Nuclear Magnetic Resonance), IR (Infrared Spectroscopy), and theoretical calculations researcher have strived to unravel the intricacies of remote participation, yet consensus remains elusive, impeding its practical application in polysaccharide synthesis.
In this study, we present our investigation into the utilization of benzoyl group-modified glucosyl donors in glycosylation reactions with various acceptors, leveraging a predictive model developed in our laboratory to analyze stereoselectivity. Through meticulous experimentation, we assessed the occurrence of remote participation and compared the outcomes with those obtained using glucosyl donors bearing acetyl groups at corresponding positions.
Furthermore, we scrutinized the impact of benzoyl group derivatives in the glycosylation processes, enriching our understanding the role of remote participation.
Our workflow encompassed the synthesis of glucose acceptors and donors bearing benzoyl group substituents, carried out glycosylation reactions, a systematic evaluation of stereoselectivity and remote participation effect. The findings underscore the potential of remote participation in directing glycosylation outcomes and shed light on the modulatory influence of benzoyl group substituents on glycosylation stereochemistry. | en_US |