Demonstrates altered stereoselectivity in glycosylation using 4,6-O-benzylidine protection, suggesting a viable solution for glycoside synthesis.
The construction of β‐glycosidic linkages with the assistance of neighbouring group participation (NGP) during N ‐iodosuccinimide and trimethylsilyl trifluoromethanesulfonate‐mediated glycosylation reactions is considered one of the most reliable reactions. In this study, we demonstrated that the 4,6‐ O ‐benzylidine protection in the galactosyl thioglycoside donor can overshadow the NGP effect, furnishing the unexpected α ‐glycoside with a specific set of acceptors and donors. We synthesized an orthogonally protected galactosyl thioglycoside donor to overcome the unexpected stereoselectivity. The outcome revealed that the presence of 4,6‐ O ‐benzylidine protection on the donor moiety can alter the stereoselectivity during glycosylation in certain cases.
No takes yet. Share an insight, caveat, or question.
Pramanik et al. (2026) studied this question.
Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context: