title: The use of the o-nitrophenyl group as a protecting/activating group for 2-acetamido-2-deoxyglucose.
abstract: The o-nitrophenyl group, a protecting group with latent activation potential, was used as a protecting group for the glycosidic position. It is stable to common conditions used in synthesis and can be activated for displacement and glycoside formation by an alcohol, using zinc chloride as a catalyst. Good to excellent yields of beta-glycosides of the important amino sugar N-acetylglucosamine were obtained. A mechanism for the reaction is proposed.
authors.affiliation: Department of Chemistry, Michigan State University, 48824, East Lansing, MI, USA.
authors.forename: Gabriela
authors.initials: G
authors.lastname: Pistia-Brueggeman
authors.forename: Rawle I
authors.initials: RI
authors.lastname: Hollingsworth
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry*; D006031:Glycosylation
chemical_list: D000117:Acetylglucosamine