title: 1,2-Tans-1-dihydroxyboryl benzyl S-glycoside as glycosyl donor.
abstract: Activated by NBS, readily available 1,2-trans-1-dihydroxyboryl benzyl S-glycosides served as glycosyl donors and reacted with certain simple alcohol acceptors to produce pure 1,2-cis-O-glycosides in moderate yields. The boronic acid moiety was revealed essential in the glycosylation for product formation and good anomeric ratio. The preliminary model reactions suggested that glycosyl aryl boronic acids could be used for stereoselective glycosylation.
authors.affiliation: School of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China; Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China.
authors.forename: Xiao
authors.initials: X
authors.lastname: Liu
authors.affiliation: Sinochem Jiangsu Co, Ltd, 22F Jincheng Dasha, 216 Longpan Zhonglu, Baixia Qu, Nanjing 210002, PR China.
authors.forename: Bingbing
authors.initials: B
authors.lastname: Zhang
authors.affiliation: School of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China; Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China.
authors.forename: Xiangying
authors.initials: X
authors.lastname: Gu
authors.affiliation: School of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China.
authors.forename: Guohua
authors.initials: G
authors.lastname: Chen
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China.
authors.forename: Lin
authors.initials: L
authors.lastname: Chen
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China.
authors.forename: Xin
authors.initials: X
authors.lastname: Wang
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China.
authors.forename: Bing
authors.initials: B
authors.lastname: Xiong
authors.affiliation: School of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China. Electronic address: youqidong@gmail.com.
authors.forename: Qi-Dong
authors.initials: QD
authors.lastname: You
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China. Electronic address: chenyuelei@gmail.com.
authors.forename: Yue-Lei
authors.initials: YL
authors.lastname: Chen
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China. Electronic address: jkshen@simm.ac.cn.
authors.forename: Jingkang
authors.initials: J
authors.lastname: Shen
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001897:Boronic Acids; D006027:Glycosides
keywords: Ate complex; Boronic acid; Glycosylation; S-Glycoside; Stereoselective