Cobalt-Catalyzed Highly α-Stereoselective Glycosylation of Glycals
Xing-Le Liu1, Qiu-Qi Mu2, Li Xu3
1School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi'an, Shaanxi 710072, P. R. China.
Abstract:
Following the satisfactory catalytic performance of cobalt in the C-glycosylation of glycals, further study of cobalt's application values was performed under mild conditions, leading to a range of highly α-stereoselective 2,3-unsaturated O-, S-, and N-glycosides. The synthetic potential of the developed protocol was underscored by the late-stage functionalization of pharmaceutically relevant molecules including the canagliflozin derivative (a potential candidate for treating type 2 diabetes and alleviating pathological aging). Furthermore, control experiments were conducted to elucidate a reasonable mechanism and rule out the pathway involving the configuration conversion between α- and β-anomers.
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