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Utilisation du triflate de fer(III) en glycosylation sous activation micro-ondes ou en flux continu

Abstract : Oligosaccharides and glycoconjugates are involved in numerous biological events. However, their synthesis is generally more complex than for other biomolecules. The main challenge is often the generation of the glycosidic bond. For this reason, it is still important to develop efficient and stereoselective glycosylations, which afford glycosides in significant amounts using new donors. These reactions are even more attractive if the promoter used is cheap, non-toxic and environmentally friendly, like iron salts. In this context, the direct synthesis of b-glycosides of N-acetyl-D-glucosamine using catalytic iron triflate(III) has been developed. This glycosylation can be performed under microwave irradiation or in continuous flow. The microwave-assisted conditions were then extended to the synthesis of complex N-glycan mimics. This synthesis is based on a polyglycosylation reaction using an iron(III) triflate catalysis coupled to another glycosylation or a click reaction to introduce a functionalized linker. Finally, an a-mannosylation promoted by iron(III) triflate has been developed. This glycosylation, performed under microwave irradiation, is completely stereoselective, even without neighbouring group participation.
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Amandine Xolin. Utilisation du triflate de fer(III) en glycosylation sous activation micro-ondes ou en flux continu. Chimie organique. Université Paris-Saclay, 2015. Français. ⟨NNT : 2015SACLS076⟩. ⟨tel-01660118⟩

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