Synthesis of the tetrasaccharide O-α-L-fucopyranosyl-(1 → 2)-[O-α-D-galactopyranosyl-(1 → 3)]-O-β-D-galactopyranosyl-(1 →4)-2-acetamido-2-deoxy-D-glucopyranose, the antigenic determinant of human blood-group B (type 2)

Add time:08/31/2019    Source:sciencedirect.com

Treatment of benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-β-D-galacto-pyranosyl-α-D-glucopyranoside with benzaldehyde in the presence of zinc chloride, followed by regioselective benzoylation (N-benzoylimidazole in dichloromethane) provided crystalline benzyl 2-acetamido-4-O-(3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside. Condensation of this disaccharide with 2,3,4-tri-O-benzyl-l-O-(N-methylacetimidyl)-β-L-fucopyranose in nitromethane in the presence of p-toluenesulfonic acid and molecular sieves 4 Å gave benzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1 → 2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1 → 4)-2- acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside. Debenzoylation, followed by condensation with 2,3,4,6-tetra-O-benzyl-l-O-(N-methylacetimidyl)-β-D-galactopyranose under the same conditions provided a tetrasaccharide derivative that was catalytically hydrogenolyzed into the title compound

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