Abstract

Derivatives of enose‐ and ynosephosphonates and related compounds. Preliminary communicationThe 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 1H‐ and 13C‐NMR. data relative to the new types of phosphorus‐containing sugar derivatives synthesized are given.

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