title: Photoinduced C-S Bond Cleavage of Thioglycosides and Glycosylation.
abstract: A glycosyl coupling reaction via photoinduced direct activation of thioglycosides and subsequent O-glycosylation in the absence of photosensitizer was developed for the first time. This reaction underwent a selectively homolytic cleavage of a C-S bond to generate a glycosyl radical, which was oxidized to an oxacarbenium ion by Cu(OTf)2, and a sequential O-glycosylation. A wide range of glycosides were synthesized in moderate to excellent yield using sugars, amino acids, or cholesterol as the acceptors.
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: Run-Ze
authors.initials: RZ
authors.lastname: Mao
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road No. 38, Beijing 100191, China.|College of Science, Northwest A&F University , Yangling, Shaanxi 712100, China.
authors.forename: Fan
authors.initials: F
authors.lastname: Guo
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.
authors.forename: Qin
authors.initials: Q
authors.lastname: Li
authors.affiliation: College of Science, Northwest A&F University , Yangling, Shaanxi 712100, China.
authors.forename: Jinyou
authors.initials: J
authors.lastname: Duan
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: Xin-Shan
authors.initials: XS
authors.lastname: Ye
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D055668:Photochemical Processes; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D006027:Glycosides; D013865:Thioglycosides