275824-49-2

Upstream product

• 275824-46-9 methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate 
• 213401-74-2 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose 
• 275824-48-1 methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate 

Relevant academic research and scientific papers

Syntheses of chondroitin 4- and 6-sulfate pentasaccharide derivatives having a methyl β-D-glucopyranosiduronic acid at the reducing end

The syntheses are reported of β-D-GlcpA-(1→3)-β-D-GalpNAc-(1→4)-β-D-GlcpA-(1→3)-β-D-GalpNAc-(1→4)-β-D-GlcpA-(1→OMe), O-sulfonated at C-4 or C-6 of the aminosugar moieties, which represent structural elements of chondroitin 4- and 6-sulfate proteoglycans. Starting from a synthetic disaccharide glycosyl acceptor, the stepwise or blockwise construction of the sugar backbone with appropriate synthons led to a pentasaccharide tetraol, which was used as a common intermediate. Selective 6-O-sulfonation of this tetraol, followed by saponification, gave the 6-sulfate derivative, whereas selective 6-O-benzoylation, followed by O-sulfonation and saponification, afforded the 4-sulfate derivative as their sodium salts. Copyright (C) 2000 Elsevier Science Ltd.