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Réactivité des glyconitriles vis-à-vis d’organométalliques : accès à des céto-C-glycosides précurseurs de C-glycoconjugés

Abstract : Glycoconjugates, an important series of organic molecules, are fundamental to many important biological processes such as inflammation, signal transduction, fertilization, bacterial-cell or cell-cell adhesion, virus-cell recognition and immune response…The use of such compounds as drug is limited by the significant hydrolysis occurring in physiological medium or in acidic conditions. Thus, more stable C-glycoconjugates syntheses have to be developed.A new strategy for the synthesis of C-glycoconjugates via acyl-C-glycosides precursors is described from gluco-, galacto- or manno-nitriles. First, the reactivity of O-perbenzylated glyconitriles towards various activated organozinc reagents led to various functionalized keto-C-glycosides. However, with Grignard reagents, a mixture of the corresponding compound along with glycal occurring from the elimination of benzyloxy group located in position 2 is observed. To prevent such elimination, 2-hydroxyglyconitrile was prepared. With organomagnesium or organolithium reagents, these glyconitriles led to various glyconitriles in good yieds. It is noteworthy that organolitium reagents were more efficient, leading to better yields in glucose and galactose series.With these keto derivatives in hands, the transformation of the keto group into methylene, gem-difluorine, alcool…. was performed on a galatose-derived ketone as a model for the preparation of more complex C-glycosides. Moreover, the application of the methodology was applied to the synthesis of original C-glycoconjugates as potential SGLT-2 or glycogen phosphorylase inhibitors, thereby validating the synthetic strategy.
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Idriss Ella Obame. Réactivité des glyconitriles vis-à-vis d’organométalliques : accès à des céto-C-glycosides précurseurs de C-glycoconjugés. Chimie organique. Université du Maine, 2016. Français. ⟨NNT : 2016LEMA1042⟩. ⟨tel-02372800⟩

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