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Synthesis and Biological Properties of N-Acetyl-4-deoxy-D-neuraminic Acid

✍ Scribed by Heinz-Werner Hagedorn; Reinhard Brossmer

Publisher: John Wiley and Sons
Year: 1986
Tongue: German
Weight: 412 KB
Volume: 69
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19860690837

No coin nor oath required. For personal study only.

✦ Synopsis

N-Acetylneuraminic acid (1) can be transformed into the methyl a-u-ketoside 2 which, by reaction with methanesulfonyl chloride, yields the corresponding 4-0 mesylate 3 and the 4.7-di-0 -mesylate 4 as a by-product. Compound 3 reacts with Nal giving the 4-dcoxy-4-iodo compound 5 with cquatorial orientation of the I-atom. As second product, the dihydrooxazole 6 is produced. Catalytic hydrogenation of 5 is followed by ester cleavage and removal of the isopropylidene group yielding the methyl r-D-ketoside 8 which affords the title compound, N-acetyl-4-deoxyncuraminic acid (9), by reaction withfbwlplague oirus sialidasc. Further biochemical activities of 8 and 9 are reported.

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