title: AuCl3-AgOTf promoted O-glycosylation using anomeric sulfoxides as glycosyl donors at room temperature.
abstract: Activation of sulfoxide as glycosyl donors using AuCl3/AgOTf reagent system has been described. Under optimal reaction conditions, both armed and disarmed glycosyl sulfoxide donors were found to react with a range of primary, secondary, and tertiary alcohol acceptors, and sugar derived glycosyl acceptors to afford the corresponding glycosides in moderate to good yields with predictable selectivity. The reactions are quick (20-60 min), facile at room temperature and the reactions conditions tolerate acid sensitive groups.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur 208 016, India.
authors.forename: Ashokkumar
authors.initials: A
authors.lastname: Palanivel
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur 208 016, India.
authors.forename: Ande
authors.initials: A
authors.lastname: Chennaiah
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur 208 016, India.
authors.forename: Sateesh
authors.initials: S
authors.lastname: Dubbu
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur 208 016, India.
authors.forename: Asadulla
authors.initials: A
authors.lastname: Mallick
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur 208 016, India. Electronic address: vankar@iitk.ac.in.
authors.forename: Yashwant D
authors.initials: YD
authors.lastname: Vankar
mesh_terms: D055731:Carbohydrate Biochemistry / Q000379:methods*; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D017612:Gold Compounds / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry*; D013696:Temperature
chemical_list: D006027:Glycosides; D017612:Gold Compounds; D008698:Mesylates; D013454:Sulfoxides; C038016:gold chloride; C012077:trifluoromethanesulfonic acid
keywords: Anomeric sulfoxides; Gold(III) chloride; O-glycosylation; Silver triflate