The use of the o-nitrophenyl group as a protecting/activating group for 2-acetamido-2-deoxyglucose.
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.
Pistia-Brueggeman
Gabriela
G
Department of Chemistry, Michigan State University, 48824, East Lansing, MI, USA.
Hollingsworth
Rawle I
RI
D000117:Acetylglucosamine / Q000737:chemistry*; D006031:Glycosylation
D000117:Acetylglucosamine