Gold-and Silver-Catalyzed Glycosylation with Pyranone Glycosyl DonorsAn Efficient and Diastereoselec

来源 :第五届岭南有机化学论坛暨华南理工大学-兰州大学有机化学双边论坛 | 被引量 : 0次 | 上传用户:wintelchia
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The O-glycosylation method has been of particular interest due to the rapid development of synthetic and biological studies of oligosaccharides and natural products containing sugar motifs.A variety of glycosylation methods have been developed such as using glycosyl halides,thioglycosides,1-O-acyl sugars,orthoesters,1-O-and S-carbonates,glycosyl imidates,4-pentenyl glycosides,phosphate/phosphite derivatives,sulfoxides,1-O-silylated glycosides,1,2-anhydrosugars,1-hydroxyl sugars,glycals,and glycosyl ortho-alkynylbenzoates as glycosyl donors.However,to our knowledge,most of glycosyl donors are unable to be activated with a catalytic amount of promoters.Development of a novel O-glycosylation method,especially activated with catalysts,is still in demand.Herein,we describe a mild,efficient and diastereoselective Au(Ⅲ)-and Ag(Ⅰ)-catalyzed O-glycosylation with pyranones as the glycosyl donors,and the reactions smoothly give α-anomers in good yields with good diastereoselectivities under mild conditions.(Scheme 1).
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