title: A new C(1)-auxiliary for anomeric stereocontrol in the synthesis of alpha-sialyl glycosides.
abstract: The installation of the novel N,N-dimethylglycolamide ester auxiliary onto the C(1)-position of protected neuraminic acid donors allows for the exploitation of C(1)-neighboring group participation to generate sialoside conjugates with good to excellent alpha-selectivity under a variety of sialylation protocols, including those that would otherwise lead to nonselective or beta-selective sialoside products.
authors.affiliation: Department of Chemistry, University of Illinois, Urbana, IL 61801, USA.
authors.forename: J M
authors.initials: JM
authors.lastname: Haberman
authors.forename: D Y
authors.initials: DY
authors.lastname: Gin
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D009438:Neuraminic Acids / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D007202:Indicators and Reagents; D009438:Neuraminic Acids