Préparation de dérivés de sucres acétyléniques terminaux et d'acides ynuroniques par réaction de Wittig. Note de laboratoire |
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Authors: | Jean M J Tronchet Alain P Bonenfant Franoise Perret Alberto Gonzalez Jean-Bernard Zumwald Ernesto M Martinez Bruno Baehler |
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Institution: | Jean M. J. Tronchet,Alain P. Bonenfant,Françoise Perret,Alberto Gonzalez,Jean-Bernard Zumwald,Ernesto M. Martinez,Bruno Baehler |
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Abstract: | Synthesis of Terminal Acetylenic Sugars Derivatives and Ynuronic Acids Derivatives by Use of a Wittig Reaction The method described for the preparation of terminal acetylenic sugars presents two advantages over earlier procedures: no new asymmetric center is created and the chain can be extended by one or more C-atoms. The method also allows preparation of ynuronic acids. The aldehydosugars derivatives 1–7 gave in good to excellent yields the corresponding gem-dibromoenoses 8–14 from which either the terminal acetylenic sugars derivatives 15–21 or the ynuronic acids 22–24 were easily prepared. A few examples of 1,3-dipolar cycloadditions (leading to 28–30 ) with these acetylenic sugar derivatives are also described. |
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