Regioselective Synthesis of Derivatives of L-Idopyranuronic Acid: A Key Constituent of Glycosaminoglycans

Authors
Vlahov, Iontcho R.
Linhardt, Robert J.
ORCID
https://orcid.org/0000-0003-2219-5833
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Other Contributors
Issue Date
1995-11-13
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Degree
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Full Citation
Regioselective Synthesis of Derivatives of L-Idopyranuronic Acid: A Key Constituent of Glycosaminoglycans, I. R. Vlahov, R. J. Linhardt, Tetrahedron Letters, 36, 8379-8382, 1995.
Abstract
Synthesis of new and potentially universal l-idopyranuronic glycosyl-donor and/or -acceptor 13 was performed starting from d-glucofuranurono-6,3-lactone 1. After simple C-5-epimerization, C-1thioacetalization and regioselective p-methoxybenzylidenation to the hydroxylactone 6, the lactone ring was opened. The resulting diolamide stereoselectively protected, providing compound 7. Regioselective reductive cleavage of the 1,3-dioxane ring and subsequent deprotection afforded the target molecule 13.
Description
Tetrahedron Letters, 36, 8379-8382
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Department
The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
Publisher
Relationships
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Tetrahedron Letters
https://harc.rpi.edu/
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