title: Templated Oligosaccharide Synthesis: Driving Forces and Mechanistic Aspects.
abstract: We previously communicated that high α-selectivity that can be achieved in intramolecular glycosylations using a rigid bisphenol A template supplemented with linkers of various lengths. Herein, we present our investigation of the mechanistic aspects of the templated synthesis that helped to design an improved template-linker combination. We demonstrate that bisphenol A as the template in combination with phthaloyl linker allows for superior stereoselectivity and yields in glycosylations. Several mechanistic studies explore origins of the enhanced stereoselectivity and yields achieved using the phthaloyl linker.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
authors.forename: Xiao G
authors.initials: XG
authors.lastname: Jia
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
authors.forename: Papapida
authors.initials: P
authors.lastname: Pornsuriyasak
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
authors.forename: Alexei V
authors.identifier: 0000-0003-3515-212X
authors.initials: AV
authors.lastname: Demchenko
mesh_terms: D001559:Benzhydryl Compounds / Q000737:chemistry; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D009844:Oligosaccharides; D010636:Phenols; C006780:bisphenol A; D000098826:Bisphenol A Compounds