Toward the modular synthesis of glycosaminoglycans: synthesis of hyaluronic acid disaccharide building blocks using a periodic acid oxidation

ER Palmacci, PH Seeberger

Index: Palmacci, Emma R.; Seeberger, Peter H. Tetrahedron, 2004 , vol. 60, # 35 p. 7755 - 7766

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Citation Number: 29

Abstract

The synthesis of two differentially protected GluNAc-β (1→ 4)-GluA and GluA-β (1→ 3)- GluNAc disaccharide modules for the solid-phase assembly of hyaluronic acid are described. A periodic acid/chromium trioxide oxidation was the key transformation to facilitate access to the glucuronic acid moiety from glucose and should find wide application in the oxidation of primary alcohols.