ChemInform Abstract: Chemical Synthesis of β-D-GlcpA(2SO4)-(1→3)-D-GalpNAc(6SO4), the Disaccharide Repeating Unit of Shark Cartilage Chondroitin Sulfate D, and of Its Methyl β-D-Glycoside Derivative.
Abstract
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ChemInform Abstract
Title compounds (XII) are prepared via β-linked disaccharides (XI) obtained by coupling of glycosyl acceptors (IX) with glucuronyl donor (X) in a stereocontrolled manner. The synthesis of acceptors (IX) involves the stereoselective glycosylation of glucopyranose (I), selective inversion of configuration at C-4, benzylation at O-4, and final transformation of diesters (VII). Unexpected pyranose→furanose ring contraction to afford furanose (XIII) as well as formation of 3,6-anhydro-derivative (XIV) are also reported.
