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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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Published in: | Carbohydrate research 1972, Vol.23 (2), p.243-249 |
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Main Authors: | , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 0008-6215 1873-426X |
DOI: | 10.1016/S0008-6215(00)88030-1 |