Abstract
Glycosylation reactions of the ethylthio, bromo and chloro derivatives of 1-deoxy-1-ethoxysulfonyl-hept-2-ulopyranose were studied applying different acceptors under different conditions. Elimination side-reactions affording exo- and endoglycals occured in all cases, however, with different proportions. Glycosyl chloride donor was applied to glycosylate a trisaccharide acceptor obtaining a new sulfonic acid mimetic of the sialyl Lewis X tetrasaccharide in high yield.
Copyright © 2011 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Inflammatory Agents / chemical synthesis*
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Anti-Inflammatory Agents / metabolism
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Anti-Inflammatory Agents / pharmacology
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Biomimetics / methods*
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Glycosides / chemical synthesis*
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Glycosides / metabolism
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Glycosides / pharmacology
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Glycosylation
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Humans
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Inflammation / drug therapy
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Inflammation / immunology
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Leukocytes / chemistry
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Leukocytes / metabolism
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Ligands
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Oligosaccharides / chemical synthesis*
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Oligosaccharides / metabolism
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Oligosaccharides / pharmacology
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Protein Binding / drug effects*
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Selectins / chemistry
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Selectins / metabolism*
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Sialyl Lewis X Antigen
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Sulfonic Acids / chemistry
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Trisaccharides / chemistry
Substances
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Anti-Inflammatory Agents
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Glycosides
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Ligands
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Oligosaccharides
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Selectins
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Sialyl Lewis X Antigen
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Sulfonic Acids
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Trisaccharides