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Deoxy-nitrosugars. 16th Communication. Synthesis of N-acetyl-4-deoxyneuraminic acid

✍ Scribed by Franz Baumberger; Andrea Vasella

Publisher
John Wiley and Sons
Year
1986
Tongue
German
Weight
447 KB
Volume
69
Category
Article
ISSN
0018-019X

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✦ Synopsis

The synthesis of 5-acetamido-4-deoxyneuraminic acid (1) is described. Acetylation of a mixture of the epimeric triols 4 and 5 gave the tetraacetates 7 and 8 (Scheme I). Ozonolysis of a mixture of these acetates followed by base-promoted B-elimination led to the ( E ) -configurated a,B-unsaturated keto ester 10, which was hydrogenated to give the saturated keto ester 11. Saponification of 11 and hydrolytic removal of the benzylidene group followed by anion-exchange chromatography gave the 5-acetamido-4-deoxyneuraminic acid (1, Scheme 1 and 2). De-0-acetylation (NaOMe/MeOH) of the keto ester 11 gave a mixture of the tert-butyl ester 12 and the methyl ester 13, which were converted to tert-butyl N-acetyl-4-deoxyneuraminate (14) and to methyl N-acetyl-4-deoxyneuraminate (15), respectively. Hydrogenolysis of the benzylidene acetalll followed by de-0-acetylation gave the pentahydroxy ester 16.

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