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

Article abstract of DOI:10.1016/0040-4039(95)01810-5

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-1-thioacetalization 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.