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Synthesis of O-β-d-galactopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→6)-d-mannopyranose by Jan Arnarp; Jörgen Lönngren; H»kan Ottosson is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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Several syntheses of oligosaccharides derived from the complex type (N-acetylo-lactosamine type) of carbohydrate portions' of glycoproteins have been reported'-'\_ We now report -on the synthesis of 0-j?-D-galactopyranosyl-(l-,4)-0-(2-acetamido-2-deoxy-/3-D-glucopyranosyl)-(l-+6)-D-mannopyranose (1). This trisaccharide is part of the most highly branched, complex type of carbohydrate portion?. Benzyl 6-O-triphenylmethyl-cr-D-mannopyranoside'" was benzylated by using sodium hydride-benzyl bromide, to give, after chromatography on silica gel, benzyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-cx-D-mannopyrannopyranoside (2) in 78 % yield. 3,6-Di-O-acetyl-2-deoxy-2-phthalimidc~-4-O-(2,3,4,6-tetra-O-acetyl-~-~-galactopyranosyl)+D-glucopyranosyl bromide3v4 (3) and mannoside 2 were condensed in nitromethane by using silver trifluoromethanesulfonate as promoter under conditions similar to those described by Bredereck and co-workers'r. After chromatography on silica gel, the trisaccharide derivative 4 was obtained in 63 '4 yield. The 2-deoxy-2phthalimido group in 4 was exchanged for a 2-acetamido-2-deoxy group by treatment with hydrazine hydrate I2 followed by acetic anhydride-pyridine, to give

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Author

Jan Arnarp; Jörgen Lönngren; H»kan Ottosson

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1981

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)