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Etude comparative de la réactivité des β-lactones et β-thiolactones. Synthèse stéréosélective d’α-C- et S-glycosides à partir de dérivés de l’acide N-acétylneuraminique

Abstract : Β-Lactones are present in many biologically active natural products; consequently, much attention has been focused on these compounds concerning structural properties as well as reactivity, unlike β-thiolactones. In order to compare these two compounds families, we have studied their thermal stability investigating the rate of CO2 and COS extrusion. Reactions were monitored by UV-mass spectrometry starting from di-, tri- and tetrasubstituted β-lactones and the corresponding β-thiolactones, in two different solvents (one polar, the other apolar). Using the same strategy, we worked on heterocycles opening by various nucleophiles. We have also studied the competitive kinetic formation of β-(thio)lactones from a common intermediate. These investigations permitted to show the similarities between these two families and revealled the possible use of β-thiolactones as β-lactone surrogates. O-Sialosides are present in many biological processes but are sensitive to enzymatic hydrolysis. We have worked on N-acetylneuraminic acid derivatives to develop a new method leading to α-selective C- and S-glycosylations, which is efficient in spite of the presence of a withdrawing group at C2 and methylene at C3 which increase glycal formation. This method leads to excellent yield and selectivity and could find applications on glycomimetic synthesis.
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Amandine Noël. Etude comparative de la réactivité des β-lactones et β-thiolactones. Synthèse stéréosélective d’α-C- et S-glycosides à partir de dérivés de l’acide N-acétylneuraminique. Autre. Université Paris Sud - Paris XI, 2012. Français. ⟨NNT : 2012PA112274⟩. ⟨tel-00912334⟩

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