Formation of glycosyl trichloroacetamides from trichloroacetimidate donors occurs through an intermolecular aglycon transfer reaction

Vrande, K.N.A. van de; Filippov, D.V.; Codee, J.D.C. (2023)

Article / Letter to editor

To probe the reaction mechanism, underlying the rearrangementofoft-used trichloroacetimidate glycosyl donors into the correspondinganomeric trichloroacetamides, we have used a combination of C-13- and N-15-labeled glycosyl trichloroacetimidate donorsin a series of crossover experiments. These unambiguously show thattrichloroacetamides are formed via an intermolecular aglycon transfermechanism. This insight enables the design of more effective glycosylationprotocols, preventing the formation of dead-end side products.

• All authors: Vrande, K.N.A. van de; Filippov, D.V.; Codee, J.D.C.
• Date: 2023-08-14
• Journal: Organic Letters
• Volume: 25
• Issue: 33
• Pages: 6128–6132
• DOI: doi:10.1021/acs.orglett.3c02196
• Link: https://pubs.acs.org/doi/10.1021/acs.orglett.3c02196