title: S-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide Synthesis via Active-Latent, Armed-Disarmed, Selective, and Orthogonal Activations.
abstract: This article describes the development of S-benzimidazolyl (SBiz) imidates as versatile building blocks for oligosaccharide synthesis. The SBiz imidates have been originally developed as a new platform for active-latent glycosylations. This article expands upon the utility of these compounds. The application to practically all common concepts for the expeditious oligosaccharide synthesis including selective, chemoselective, and orthogonal strategies is demonstrated. The strategy development was made possible thanks to our enhanced understanding of the reaction mechanism and the modes by which SBiz imidates interact with various promoters of glycosylation.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Hasty
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
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, United States.
authors.forename: Nigam P
authors.initials: NP
authors.lastname: Rath
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: D001562:Benzimidazoles / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006031:Glycosylation; D007096:Imidoesters / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001562:Benzimidazoles; D007096:Imidoesters; D009844:Oligosaccharides