| Abstract: | 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 1H- and 13C-NMR. data relative to the new types of phosphorus-containing sugar derivatives synthesized are given. |
