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Phosphonic-Acid Analogues of the N-Acetyl-2-deoxyneiiraniinic Acids: Synthesis and Inhibition of Vibrio cholerae Sialidase

✍ Scribed by Kurt Wallimann; Andrea Vasella


Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
987 KB
Volume
73
Category
Article
ISSN
0018-019X

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✦ Synopsis


ing an equatorial COOH group is a moderatly strong inhibitor of the N-acetylneuraminidases from Vibrio cholerae and fowl plague virus, whilst the epimeric acid possessing axial COOH and HO-C(4) groups is not [2].


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## Abstract The peracetylated methyl ester 1 of N‐acetylneuraminic acid was transformed into the oxazoline derivative 2, which was hydrogenated with Pd/C/H~2~ to give the 4‐deoxy‐Neu5Ac2en derivative 3. Acid cleavage of the oxazoline 2 by trifluoroacetic acid (THF) gave the 4‐epi‐Neu5Ac2en derivati