title: Glycosylation of Nucleosides.
abstract: Nucleoside O-glycosylation represents an archetypal problem in chemical selectivity, inasmuch as the nucleobase (an undesired site of reaction) is usually more nucleophilic than the hydroxyl (the desired site of reaction). Optimized reaction conditions have been developed for the efficient O-glycosylation of nucleoside hydroxyls. Both thioglycoside and Schmidt imidate donors (1.5 equiv) have been employed successfully. Interference by the nucleobase is minimized by the use of indium(III) triflate as the donor activating reagent; the In(OTf)3 serves to promote apparent transfer of the donor glycosyl moiety from nucleobase to hydroxyl. Glycosylation of uridine triacetate gives products resulting from O- and N-glycosylation of the pyrimidine ring.
authors.affiliation: Department of Chemistry & Chemical Biology, Rutgers The State University of New Jersey , 610 Taylor Road, Piscataway, New Jersey 08854, United States.
authors.forename: Yonglian
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Department of Chemistry & Chemical Biology, Rutgers The State University of New Jersey , 610 Taylor Road, Piscataway, New Jersey 08854, United States.
authors.forename: Spencer
authors.initials: S
authors.lastname: Knapp
mesh_terms: D006031:Glycosylation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C522942:Indium(III) trifluoromethanesulfonate; D009705:Nucleosides; D009942:Organometallic Compounds; D011743:Pyrimidines