Bismuth-Catalyzed Stereoselective 2-Deoxyglycosylation of Disarmed/Armed Glycal Donors
Manoj Kumar1, Aakanksha Gurawa1, Nitin Kumar1
1Carbohydrate Chemistry Research Laboratory (CCRL), Department of Chemistry, MNIT, Jaipur 302017, India.
Abstract:
Bi(OTf)3 promoted direct and highly stereoselective glycosylation of "disarmed" and "armed" glycals to synthesize 2-deoxyglycosides has been reported. The tunable and solvent-controlled chemoselective activation of deactivated glycal donors distinguishing the competitive Ferrier and 1,2-addition pathways was discovered to improve substrate scope. The practical versatility of the method has been amply demonstrated with the oligosaccharide syntheses and 2-deoxyglycosylation of high-value natural products and drugs.
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