Application of a radical reaction to the synthesis of l-iduronic acid derivatives from d-glucuronic acid analogues☆

Add time:08/20/2019    Source:sciencedirect.com

Commercially available d-glucofuranurono-6,3-lactone was transformed into the known, crystalline methyl (5R)-1,2,3,4-tetra-O-acetyl-5-C-bromo-β-d-glucopyranuronate (3) in three steps. Reduction with tributyltin hydride gave crystalline methyl 1,2,3,4-tetra-O-acetyl-α-l-idopyranuronate (4) in ∼30% yield, together with the crystalline methyl 1,2,3,4-tetra-O-acetyl-β-d-glucopyranuronate (1, 63.5%) which may be separated and converted back by Ferrier's photobromination into 3. This procedure provides the first practical and expeditious conversion of d-glucuronic acid into d-iduronic acid by epimerization. Acetate 4 was converted in quantitative yield into methyl (2,3,4-tri-O-acetyl-α-l-idopyranosyl bromide)-uronate (22), and then into methyl 3,4-di-O-acetyl-β-l-idopyranuronate 1,2-(methyl orthoester) (23), which are useful compounds for glycosylation reactions. Various β-d-glucuronic acid derivatives have been epimerized to α-l-iduronic acid analogues by this novel procedure.

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