Premium
Dérivés d'énose‐ et d'ynosephosphonates et composés voisins . Communication préliminaire
Author(s) -
Tronchet Jean M. J.,
Bonenfant Alain P.,
Pallie Kemal Deen,
Habashi Ford
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620528
Subject(s) - chemistry , derivative (finance) , electrophile , halogenation , phosphorus , cycloaddition , sugar , medicinal chemistry , organic chemistry , glycoside , stereochemistry , catalysis , financial economics , economics
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.