title: Access to ring-expanded analogues of 2-amino sugars.
abstract: Ring-expanded 2-N-acetylamino sugar analogs of D-glucose, D-galactose, and D-mannose have been prepared by a new synthetic route. Aspects of the highly substituted alpha-amino aldehyde intermediates made them central to the approach. First, they were accessed via diastereoselective addition of a vinyl Grignard onto protected glycosyl amines. Also, the sterics of the bis-protected amine favored the formation of only one glycoside anomer. The new analogues reported here should prove useful in the development of tools to investigate the role of 2-amino sugars in biology.
authors.affiliation: Department of Chemistry, University of Connecticut, 55 North Eagleville Road U-3060, Storrs, Connecticut 06269, USA.
authors.forename: Jaideep
authors.initials: J
authors.lastname: Saha
authors.forename: Mark W
authors.initials: MW
authors.lastname: Peczuh
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D013237:Stereoisomerism
chemical_list: D000588:Amines; D000606:Amino Sugars