Abstract
O-(α- dMannopyranosyl)-(1 → 2)- O(α- d-mannopyranosyl)-(1 → 3)- O-[(α- d-mannopyranosyl)-(1 → 2)- O-(α- d-mannopyranosyl)-(1 → 6)]- O-(α- d-mannopyranosyl)-(1 → 6)- O-(β- d-mannopyranosyl)-(1 → 4)- O-(2-acetamido-2-deoxy-β- d-glucopyranosyl)-(1 → 4)-2-acetamido-2-deoxy-glucopyranose, an octasaccharide fragment of high-mannose type glycan of glycoproteins, was synthesized. Crucial glycosylation of trisaccharide intermediate, benzyl O-(2,4-di- O-benzyl-β- d-mannopyranosyl)-(1 → 4)- O-(2-acetamido-3,6-di- O-benzyl-2-deoxy-β- d-glucopyranosyl)-(1 → 4)-2-acetamido-3,6-di- O-benzyl-2-deoxy-β- d-glucopyranoside, was successful only with a di- O-acetyltetradeca- O-benzyl- d-mannopentaosyl chloride. The use of the corresponding hexadeca- O-acetyl- d-mannopentaosyl bromide did not give the desired product.
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