title: Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot.
abstract: A new series of superarmed glycosyl donors has been investigated. It was demonstrated that the S-ethyl leaving group allows for high reactivity, which is much higher than that of equally equipped S-phenyl glycosyl donors that were previously investigated by our groups. The superarmed S-ethyl glycosyl donors equipped with a 2-O-benzoyl group gave complete β-stereoselectivity. Utility of the new glycosyl donors has been demonstrated in a one-pot one-addition oligosaccharide synthesis with all of the reaction components present from the beginning.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
authors.forename: Mithila D
authors.initials: MD
authors.lastname: Bandara
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
authors.forename: Jagodige P
authors.initials: JP
authors.lastname: Yasomanee
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
authors.forename: Nigam P
authors.initials: NP
authors.lastname: Rath
authors.affiliation: Department of Chemistry, University of Copenhagen, 2100 Copenhagen Ø, Denmark.
authors.forename: Christian M
authors.identifier: http://orcid.org/0000-0003-4661-4895
authors.initials: CM
authors.lastname: Pedersen
authors.affiliation: Department of Chemistry, University of Copenhagen, 2100 Copenhagen Ø, Denmark.
authors.forename: Mikael
authors.initials: M
authors.lastname: Bols
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
authors.forename: Alexei V
authors.identifier: http://orcid.org/0000-0003-3515-212X
authors.initials: AV
authors.lastname: Demchenko
mesh_terms: D002236:Carbohydrate Conformation; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D009844:Oligosaccharides