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Synthesis of 6-thiosialic acids and 6-thio-N-acetyl-D-neuraminic acid

✍ Scribed by H Mack; R Brossmer

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
224 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

Aldol condensation of la with potassium di-tert-butyloxaloacetate yields the two epimeric 6-thiosialic acids 2 and 3. As opposed to this, reaction between thiofuranose 6 _ and nickel (II)/oxaloacetate affords 6-thio-N-acetyl-D-neuraminic acid _Ic. Substituting sulfur for oxygen in the pyranosering drastically changes the biological properties.

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✍ Heinz-Werner Hagedorn; Reinhard Brossmer πŸ“‚ Article πŸ“… 1986 πŸ› John Wiley and Sons 🌐 German βš– 412 KB

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 orient