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Bismuth-Catalyzed Stereoselective 2-Deoxyglycosylation of Disarmed/Armed Glycal Donors.

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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… Click to show full 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.

Keywords: deoxyglycosylation disarmed; disarmed armed; catalyzed stereoselective; stereoselective deoxyglycosylation; glycal donors; bismuth catalyzed

Journal Title: Organic letters
Year Published: 2022

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