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Synthesis of a Phosphonic Acid Analogue of N-Acetyl-2,3-didehydro-2-deoxyneuraminic Acid, an Inhibitor of Vibrio cholerae Sialidase

✍ Scribed by Andrea Vasella; René Wyler

Publisher: John Wiley and Sons
Year: 1991
Tongue: German
Weight: 922 KB
Volume: 74
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19910740223

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✦ Synopsis

Obtained in five steps from N-acetylneuraminic acid (Neu5Ac) according to known procedures [3]. Zto and Ogawa indicate a ratio 12/13 of 1:4.1 [lo]. Such a neighbouring group participation [ 121 and particularly the formation of 6,8-dioxa[3.2.l]bicyclooctane structures similar to 15 have been described in some detail; see [5] and refs. cit. therein. Almost no reaction occurred in the absence of pyridine.

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