Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1388752 | Carbohydrate Research | 2008 | 8 Pages |
Abstract
To understand the contradictory results on the structure of the lipopolysaccharide isolated from a Yersinia enterocolitica O:3, both anomers of methyl 2-acetamido-2,6-dideoxy-d-xylo-hexopyranosid-4-ulose were prepared. The key steps of the synthetic pathway were the selective acetylation of the methyl 2-acetamido-2,6-dideoxy-α,β-d-glucopyranosides, the oxidation of the 4-position to form the keto-sugars, and deacetylation to provide the target compound. Surprisingly, the last step was accompanied by a disproportionation to give methyl 2-acetamido-2,6-dideoxy-α- and β-d-glucopyranosides and N-(5-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)acetamide as side-products.
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Authors
Sabine Borowski, Dirk Michalik, Helmut Reinke, Christian Vogel, Anna Hanuszkiewicz, Katarzyna A. Duda, Otto Holst,