Regioselective synthesis of derivatives of l-idopyranuronic acid: A key constituent of glycosaminoglycans

Iontcho R. Vlahov, Robert J. Linhardt

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

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.

Original languageEnglish
Pages (from-to)8379-8382
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number46
DOIs
StatePublished - 13 Nov 1995
Externally publishedYes

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