Regioselective Synthesis of L-Idopyranuronic Acid Derivatives:Intermolecular Aglycone Transfer Under Standard Glycosylation Conditions

Authors
Du, Y.
Linhardt, Robert J.
ORCID
https://orcid.org/0000-0003-2219-5833
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Other Contributors
Issue Date
1997
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Degree
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Full Citation
Regioselective Synthesis of L-Idopyranuronic Acid Derivatives:Intermolecular Aglycone Transfer Under Standard Glycosylation Conditions,Y. Du, R.J. Linhardt, Journal of Carbohydrate Chemistry, 16,1327-1344, 1997.
Abstract
C-1-thioacetalization of L-idofuranurono-6,3-lactone followed by regioselective p-methoxybenzylidenation at C-2 and C-4 gave the hydroxylactones 4 and 19, which were protected at C-5 with TBDMS. Lactone ring opening with methylamine followed by regioselective reductive cleavage of the 1,3-dioxane furnished acceptors 9 and 24. Intermolecular ethyl and phenyl thio group transfers were observed during the attempted preparation of disaccharide 35 through coupling reactions of either 9 or 24 with trichloroacetimidate donor 33, leading to the formation of thioglycoside of donor 33 and the thioglycoside of acceptors 9 or 24 in the furanose form. This intermolecular aglycon transfer was investigated under various glycosylation conditions. Finally, the free 4-hydroxyl groups in acceptors 9 and 24 were acetylated. Desilylation at C-5 followed by ring closure with mercuric salts afforded, in both cases, the IdopA donor and/or acceptor precursor 16.
Description
Journal of Carbohydrate Chemistry, 16,1327-1344
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Department
The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
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The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
https://harc.rpi.edu/
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