title: The mild cleavage of 2-amino-2-deoxy-D-glucoside methoxycarbonyl derivatives.
abstract: The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl(3) and triethylamine in dry THF at 60 degrees C and subsequent aqueous hydrolysis yields the free amine in 54 to 93% yields. The selective cleavage of methyl carbamates with MeSiCl(3) in the presence of a 2,2,2-trichloroethoxycarbonyl group or 2-azido glycosides affords selectively, orthogonal N-deprotected carbohydrates.
authors.affiliation: Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
authors.forename: B K
authors.initials: BK
authors.lastname: Yeung
authors.forename: S L
authors.initials: SL
authors.lastname: Adamski-Werner
authors.forename: J B
authors.initials: JB
authors.lastname: Bernard
authors.forename: G
authors.initials: G
authors.lastname: Poulenat
authors.forename: P A
authors.initials: PA
authors.lastname: Petillo
mesh_terms: D002384:Catalysis; D005960:Glucosides / Q000737:chemistry*; D006868:Hydrolysis; D008759:Methylglycosides / Q000737:chemistry*
chemical_list: D005960:Glucosides; D008759:Methylglycosides