title: Nickel-catalyzed α-glycosylation of C(1)-hydroxyl D-myo-inositol: a formal synthesis of mycothiol.
abstract: Formal synthesis of mycothiol has been developed via nickel-catalyzed α-glycosylation of the C(1)-hydroxyl group of D-myo-inositols with C(2)-N-substituted benzylideneamino N-phenyl trifluoroacetimidate donors. The pseudo-oligosaccharides were obtained in good yield and with excellent α-selectivity. Removal of the C(2)-N-2-trifluoromethylphenyl-benzylidene group under mild conditions provides a pseudo-disaccharide, completing the formal synthesis of mycothiol.
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA.
authors.forename: Matthew S
authors.initials: MS
authors.lastname: McConnell
authors.forename: Fei
authors.initials: F
authors.lastname: Yu
authors.forename: Hien M
authors.initials: HM
authors.lastname: Nguyen
mesh_terms: D002384:Catalysis; D003545:Cysteine / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007294:Inositol / Q000138:chemical synthesis / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry*; D013302:Streptomyces / Q000378:metabolism
chemical_list: D006020:Glycopeptides; C089265:mycothiol; D007294:Inositol; D009532:Nickel; D003545:Cysteine