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Ultra High Pressure as a Green and Promising Tool in Glycochemistry

[ Vol. 9 , Issue. 3 ]

Author(s):

Christine Thomassigny, Fernando Sineriz, Christine Greck and Francoise Dumas   Pages 228 - 242 ( 15 )

Abstract:


Pressure is a fundamental parameter which can accelerate reaction rates. The use of ultra high pressure (0.2-2 GPa) in organic chemistry can be particularly efficient, because it can fix problems of reactivity or regio- and stereoselectivity which could appear at ambient pressure, while being considered as an activation tool. The present review points out the last progresses in the area of glycochemistry with this technique. Selective protection or deprotection of the hydroxyl group of saccharides are described, as well as the most studied cycloaddition reactions, leading to the sugar-base structure dihydropyran or employing a sugar to enhance the stereoselectivity of the reaction. The Wittig reaction, homoallylation with allylstannane and aza-Michael reaction are also presented.

Keywords:

Ultra high pressure (UHP), glycochemistry, regio- and stereoselective synthesis, green chemistry, reactivity.

Affiliation:

Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles-St-Quentin-en-Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France.



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