title: Lactonization-mediated glycosylations and their application to oligosaccharide synthesis.
abstract: The concept of lactonization-mediated and related glycosylations led us to develop new methods of glycosylation such as the 2'-carboxybenzyl (CB) glycoside method, the glycosyl pentenoate/phenylselenyl trifluoromethanesulfonate (PhSeOTf) method, and the glycosyl aryl phthalate method. Highly stereoselective beta-mannopyranosylations were achieved by employing the CB glycoside and the glycosyl pentenoate/PhSeOTf methods. The CB glycoside method was also utilized for stereoselective 2-deoxyglycosylation, beta-arabinofuranosylation, and alpha-galactofuranosylation. In addition, these lactonization-mediated methods of glycosylation were employed for the synthesis of complex oligosaccharides. In particular, the CB glycoside method was successfully applied to the synthesis of repeating oligosaccharide subunits of the O-polysaccharide of the lipopolysaccharide from Danish Helicobacter pylori strains and Escherichia coli 077, the synthesis of oligoarabinofuranosides in mycobacterial cell walls, and the total synthesis of antineoplastic agelagalastatin.
authors.affiliation: Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University, Seoul 120-749, Korea. kwan@yonsei.ac.kr
authors.forename: Kwan Soo
authors.initials: KS
authors.lastname: Kim
authors.forename: Heung Bae
authors.initials: HB
authors.lastname: Jeon
mesh_terms: D002236:Carbohydrate Conformation; D006031:Glycosylation; D007783:Lactones / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011135:Polysaccharides, Bacterial / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D009844:Oligosaccharides; D011135:Polysaccharides, Bacterial