A new C(1)-auxiliary for anomeric stereocontrol in the synthesis of alpha-sialyl glycosides.
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.
Haberman
J M
JM
Department of Chemistry, University of Illinois, Urbana, IL 61801, USA.
Gin
D Y
DY
D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D009438:Neuraminic Acids / Q000737:chemistry; D013237:Stereoisomerism
D006027:Glycosides; D007202:Indicators and Reagents; D009438:Neuraminic Acids