Lactonization-mediated glycosylations and their application to oligosaccharide synthesis.
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.
Kim
Kwan Soo
KS
Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University, Seoul 120-749, Korea. kwan@yonsei.ac.kr
Jeon
Heung Bae
HB
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
D007783:Lactones; D009844:Oligosaccharides; D011135:Polysaccharides, Bacterial