Utilisation d'ylides du phosphore en chimie des sucres. XX. Synthèse de sucres acétyléniques et réarrangment d'intermédiaires carbénoïdes. Communication préliminaire |
| |
Authors: | Jean M J Tronchet Alberto Gonzalez Jean-Bernard Zumwald Franoise Perret |
| |
Institution: | Jean M. J. Tronchet,Alberto Gonzalez,Jean-Bernard Zumwald,Françoise Perret |
| |
Abstract: | Two novel methods for the synthesis of terminal acetylenic sugars, both involving a chain extension by one carbon unit, are described. In the first procedure, an aldehydo-sugar is treated with dibromomethylenetriphenyl-phosphorane, then with n-butyllithium and finally with water. The second method involves an one-step reaction between an aldehydo-sugar and dimethyl diazomethylphosphonate. The acetylenic sugars obtained are valuable synthetic intermediates for the preparation of heterocyclic C-nucleosides by 1,3-dipolar cycloaddition reactions and some examples of syntheses of this type are described. Treatment of keto-sugars with dimethyl diazomethylphosphonate led to an intermediate carbenoid species which reacted by insertion into a C? H bond in one case and underwent nucleophilic attack by a methoxy group in a second case. |
| |
Keywords: | |
|
|