TY - JOUR
T1 - Synthesis of methyl 2-acetamido-2,6-dideoxy-alpha- and beta-d-xylo-hexopyranosid-4-ulose, a keto sugar which misled the analytical chemists.
AU - Borowski, Sabine
AU - Michalik, Dirk
AU - Reinke, Helmut
AU - Vogel, Christian
AU - Hanuszkiewicz, Anna
AU - Duda, Katarzyna A
AU - Holst, Otto
N1 - Keywords: Acetylation; Keto Acids; Ketoses; Magnetic Resonance Spectroscopy; Molecular Structure
PY - 2008
Y1 - 2008
N2 - 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-alpha,beta-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-alpha- and beta-d-glucopyranosides and N-(5-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)acetamide as side-products.
AB - 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-alpha,beta-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-alpha- and beta-d-glucopyranosides and N-(5-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)acetamide as side-products.
U2 - 10.1016/j.carres.2008.02.001
DO - 10.1016/j.carres.2008.02.001
M3 - Journal article
C2 - 18314095
SN - 0008-6215
VL - 343
SP - 1004
EP - 1011
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 6
ER -