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Lactonization‐mediated glycosylations and their application to oligosaccharide synthesis
Author(s) -
Kim Kwan Soo,
Jeon Heung Bae
Publication year - 2008
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.20138
Subject(s) - glycosylation , glycosyl , glycoside , chemistry , stereochemistry , glycosyl donor , stereoselectivity , trifluoromethanesulfonate , biochemistry , catalysis
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 β‐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, β‐arabinofuranosylation, and α‐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. © 2008 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 8: 46–65; 2008: Published online in Wiley InterScience ( www.interscience.wiley.com ) DOI 10.1002/tcr.20138