Synthesis of a hexasaccharide that relates to the arabinogalactan epitope.
A hexasaccharide derivative of the arabinogalactan epitope, methyl beta-D-galactopyranosyl-(1-->6)-[alpha-L-arabinofuranosyl-(1-->3)]-beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranosyl-(1-->6)-[alpha-L-arabinofuranosyl-(1-->3)]-alpha-D-galactopyranoside, was synthesized efficiently using a 3+3 strategy. The key step is the preparation of the trisaccharide donor, isopropyl 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1-->6)-[2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl-(1-->3)]-2,4-di-O-benzoyl-1-thio-beta-D-galactopyranoside, from isopropyl 1-thio-beta-D-galactopyranoside using a one-pot synthesis of a 3,6-differentially protected building block.
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Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, Beijing 100085, PR China.
Yang
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Du
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Kong
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D000939:Epitopes / Q000737:chemistry*; D005685:Galactans / Q000737:chemistry*; D007544:Isopropyl Thiogalactoside / Q000737:chemistry*; D025942:Oligosaccharides, Branched-Chain / Q000138:chemical synthesis*; D014312:Trisaccharides / Q000138:chemical synthesis*
D000939:Epitopes; D005685:Galactans; D025942:Oligosaccharides, Branched-Chain; D014312:Trisaccharides; D007544:Isopropyl Thiogalactoside; C005653:arabinogalactan