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

Vlahov, Iontcho R.
Linhardt, Robert J.
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Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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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.
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.
Tetrahedron Letters, 36, 8379-8382
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The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
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Rensselaer Polytechnic Institute, Troy, NY
Tetrahedron Letters