title: Stereoselective synthesis of β-rhamnopyranosides via gold(I)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors.
abstract: Stereoselective β-rhamnopyranosylation remains a challenge, due to the unfavorable anomeric effect and steric hindrance of the C2-substituent; herein, this challenge is addressed with a gold(I)-catalyzed SN2-like glycosylation protocol employing α-rhamnopyranosyl 2-alkynyl-4-nitro-benzoates as donors.
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. byu@mail.sioc.ac.cn.
authors.forename: Yugen
authors.initials: Y
authors.lastname: Zhu
authors.affiliation: School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai 201210, China.
authors.forename: Zhengnan
authors.initials: Z
authors.lastname: Shen
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. byu@mail.sioc.ac.cn.
authors.forename: Wei
authors.initials: W
authors.lastname: Li
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. byu@mail.sioc.ac.cn.
authors.forename: Biao
authors.initials: B
authors.lastname: Yu
mesh_terms: D002384:Catalysis; D006031:Glycosylation; D006046:Gold / Q000737:chemistry*; D008968:Molecular Conformation; D009579:Nitrobenzoates / Q000737:chemistry*; D050607:Organogold Compounds / Q000737:chemistry*; D012210:Rhamnose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009579:Nitrobenzoates; D050607:Organogold Compounds; D006046:Gold; D012210:Rhamnose