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The synthesis of oligosaccharide- l-asparagine compounds. Part IV. 2-acetamido- N-( l-aspart-4-oyl)-2-deoxy-6- O-α- d-mannopyranosyl-β- d-glucopyranosylamine

The title compound, used for the chemical and biochemical synthesis of glycopeptides and as a reference substance in the structure elucidation of glycoproteins, was synthesized via two different routes. In one of these syntheses, condensation of 2,3,4,6-tetra- O-acetyl-α- d-mannopyranosyl bromide (...

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Bibliographic Details
Published in:Carbohydrate research 1972, Vol.23 (2), p.243-249
Main Authors: Shaban, Mohammed A.E., Jeanloz, Roger W.
Format: Article
Language:English
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Summary:The title compound, used for the chemical and biochemical synthesis of glycopeptides and as a reference substance in the structure elucidation of glycoproteins, was synthesized via two different routes. In one of these syntheses, condensation of 2,3,4,6-tetra- O-acetyl-α- d-mannopyranosyl bromide ( 1) with 2-acetamido-3,4-di- O-acetyl-2-deoxy-β- d-glucopyranosyl azide, or with the 3- O-acetyl azide analog, followed by acetylation, gave 2-acetamido-3,4-di- O-acetyl-2-deoxy-6- O-(2,3,4,6-tetra- O-acetyl-α- d-mannopyranosyl)-β- d-glucopyranosyl azide ( 4) in 76 and 74% yields, respectively. Catalytic reduction of 4 with Adams' catalyst, and condensation of the resulting amine with 1-benzyl N-(benzyloxycarbonyl)- l-aspartate, gave the protected derivative 10 of the title compound in 67% yield. In the other synthesis, 10 was obtained in 66% yield by condensation of 1 with 2-acetamido-3,4-di- O-acetyl- N-[1-benzyl N-(benzyloxycarbonyl)- l-aspart-4-oyl]-2-deoxy-β- d-glucopyranosylamine. Removal of the protective O-acetyl, N-(benzyloxycarbonyl), and benzyl groups gave the title compound.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(00)88030-1