title: Additive-controlled stereoselective glycosylations of 2,3-oxazolidinone protected glucosamine or galactosamine thioglycoside donors with phenols based on preactivation protocol.
abstract: Stereo-controllable glycosylation reactions of 2,3-oxazolidinone protected glucosamine thioglycoside donor with different phenol acceptors based on preactivation protocol, are described. It was found that BF3·Et2O worked as α-directing additive, while TTBP acted as β-directing additive. Simply by altering additives, either α-aryl glycosides or β-aryl glycosides were achieved in a stereoselective manner. The additives were also applied to the stereoselective glycosylation reactions of 2,3-oxazolidinone protected galactosamine donor with phenol substrates.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing 100191, China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Qin
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing 100191, China.
authors.forename: De-Cai
authors.initials: DC
authors.lastname: Xiong
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing 100191, China. Electronic address: xinshan@bjmu.edu.cn.
authors.forename: Xin-Shan
authors.initials: XS
authors.lastname: Ye
mesh_terms: D005688:Galactosamine / Q000737:chemistry*; D005944:Glucosamine / Q000737:chemistry*; D006031:Glycosylation; D023303:Oxazolidinones / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D023303:Oxazolidinones; D010636:Phenols; D013865:Thioglycosides; D005688:Galactosamine; D005944:Glucosamine
keywords: Additive; Aryl glycoside; Glycosylation; Preactivation; Stereoselectivity