Journal
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Volume 48, Issue 1, Pages 220-240Publisher
SPRINGER
DOI: 10.1007/s10593-012-0984-4
Keywords
carbohydrates; glycoconjugates; oligosaccharides; thioimidates; glycosylation; leaving group
Categories
Funding
- National Science Foundation [CHE-1058112]
- National Institute of General Medical Studies [GM077170]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1058112] Funding Source: National Science Foundation
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This review discusses the synthesis and application of glycosyl thioimidates in chemical glycosylation and oligosaccharide assembly. Although glycosyl thioimidates include a broad range of compounds, the discussion herein centers on S-benzothiazolyl (SBaz), S-benzoxazolyl (SBox), S-thiazolinyl (STaz), and S-benzimidazolyl (SBiz) glycosides. These heterocyclic moieties have recently emerged as excellent anomeric leaving groups that express unique characteristics for highly diastereoselective glycosylation and help to provide a streamlined access to oligosaccharides.
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