Highly Stereoselective Synthesis of 2-Azido-2-Deoxyglycosides via Gold-Catalyzed S_(N)2 Glycosylation  

作　　者：Yongliang Zhang Xu Ma Liming Zhang 

机构地区：[1]Department of Chemistry and Biochemistry,University of California,Santa Barbara,California 93106

出　　处：《CCS Chemistry》2023年第12期2799-2807,共9页中国化学会会刊（英文）

基　　金：the National Institutes of Health(grant nos.U01GM125289 and R35GM139640)for financial support;the National Science Foundation(grant no.MRI-1920299)for the acquisition of two Bruker NMR instruments.

摘　　要：Highly stereoselective synthesis of 2-azido-2-deoxyglucosides and 2-azido-2-deoxygalactosides is achieved via a gold-catalyzed S_(N)2 glycosylation.The glycosyl donors feature a designed 1-naphthoate leaving group containing an amide group.Upon gold activation of the leaving group,the amide group is optimally positioned to direct an S_(N)2 attack by an acceptor via H-bonding interaction.Both 2-azido-2-deoxyglucosyl/galactosyl donor anomers can undergo stereoinversion at the anomeric position,affording the opposite anomeric glycoside products with excellent levels of stereoselectivity or stereospecificity and in mostly excellent yields.This S_(N)2 glycosylation accommodates a broad range of acceptors.The utility of this chemistry is demonstrated in the synthesis of a trisaccharide featuring three 1,2-cis-2-azido-2-deoxyglycosidic linkages.

关 键 词：aminosugar GLYCOSYLATION 1 2-cis-glycosidic linkage gold catalysis directing group 

分 类 号：O62[理学—有机化学]