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Dérivés d'énose- et d'ynosephosphonates et composés voisins. Communication préliminaire

✍ Scribed by Jean M. J. Tronchet; Alain P. Bonenfant; Kemal Deen Pallie; Ford Habashi

Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
207 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis

Derivatives of enose‐ and ynosephosphonates and related compounds. Preliminary communication

The gem‐dibromo terminal enoses 1 and 7 are convenient sources of glycosylacetylenes which upon reaction with phosphorus electrophiles gave the phosphorusbearing acetylenic sugars 4, 5 and 8. Compounds 5 and 8 underwent cycloaddition reactions leading to isoxazolyl‐C‐glycosides 6 and 9 respectively. The nitroolefinic sugar derivative 11 gave upon bromination‐dehydrobromination the first example of a new kind of potentially useful synthetic intermediates, the gem‐bromonitroenose 12. The enosephosphonate 13 was also prepared from 11. The diglycosylhydroxylamine 18 represents another type of phosphorus‐bearing acetylenic sugar derivative. Some ^1^H‐ and ^13^C‐NMR. data relative to the new types of phosphorus‐containing sugar derivatives synthesized are given.

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