title: Nucleophilic catalysis of MeON-neoglycoside formation by aniline derivatives.
abstract: Neoglycosylations are increasingly being employed in the synthesis of natural products, drug candidates, glycopeptide mimics, oligosaccharide analogues, and other applications, but the efficiency of these reactions is usually limited by slow reaction times. Here, we show that aniline derivatives such as 2-amino-5-methoxybenzoic acid enhance the rate of acid-catalyzed neoglycosylation for a range of sugar substrates up to a factor of 32 relative to the uncatalyzed reaction.
authors.affiliation: Department of Chemistry, Seattle University , Seattle, Washington 98122, United States.
authors.forename: Steven A
authors.initials: SA
authors.lastname: Loskot
authors.forename: Jianjun
authors.initials: J
authors.lastname: Zhang
authors.forename: Joseph M
authors.initials: JM
authors.lastname: Langenhan
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration
chemical_list: D000814:Aniline Compounds; D006027:Glycosides; C023650:aniline