title: Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.
abstract: Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing the efficiency of the synthesis. In contrast, expeditious strategies allow for the rapid chemical synthesis of complex carbohydrates by minimizing extraneous chemical manipulations. Oligosaccharide synthesis by selective activation of one leaving group over another is one such expeditious strategy. Herein, the significant improvements that have recently emerged in the area of the selective activation are discussed. The development of orthogonal strategy further expands the scope of the selective activation methodology. Surveyed in this article, are representative examples wherein these excellent innovations have been applied to the synthesis of various oligosaccharide sequences.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri, St. Louis, One University Boulevard, St. Louis, MO 63121, USA.
authors.forename: Sophon
authors.initials: S
authors.lastname: Kaeothip
authors.forename: Alexei V
authors.initials: AV
authors.lastname: Demchenko
mesh_terms: D000080:Acetals / Q000737:chemistry; D000215:Acylation; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002625:Chemistry, Organic / Q000379:methods*; D005459:Fluorides / Q000737:chemistry; D054794:Glycomics; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D006219:Halogens / Q000737:chemistry; D006493:Heparin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D007096:Imidoesters / Q000737:chemistry; D052578:Ionic Liquids / Q000737:chemistry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013454:Sulfoxides / Q000737:chemistry; D013861:Thiocyanates / Q000737:chemistry
chemical_list: D000080:Acetals; D006027:Glycosides; D006219:Halogens; D007096:Imidoesters; D052578:Ionic Liquids; D009844:Oligosaccharides; D013454:Sulfoxides; D013861:Thiocyanates; D006493:Heparin; D005459:Fluorides