Transition metal-catalyzed approaches to functionalyze glycosyl thiols

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1st EuroCarb Young Researcher (ECYR) Workshop

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Mini symposium: Glycobiology at the LUMC and beyond

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Transition metal-catalyzed approaches to functionalyze glycosyl thiols

Samir Messaoudi 1

1 CNRS - Université Paris Sud, Châtenay Malabry, France

Thioglycosides are valuable glycomimetic derivatives that have attracted much attention as mimetics of O-glycosides. Thioglycosides are among the most important glycomimetics reported to date due to their powerful activities. Owing to their importance, building up methods for their construction has drawn considerable attention. However, the classical methods of their synthesis presenting many shortcomings such as the use of harsh acidic media, and are generally limited in substrate scope. Therefore, metal-catalyzed coupling of thiosugars with halogenated electrophiles can be a superior and highly versatile approach to the sunthesis of thioglycosides.

The palladium‐catalyzed Buchwald–Hartwig–Migita cross‐coupling reaction has become an effective tool in industrial and academic research giving acces to natural products and novel materials as well as a wide number of pharmaceuticals currently on the market. Advances in this coupling reactions have been driven by the discovery of a new class of ligands, which are able to promote reactions with a variety of substrates including nitrogen‐, sulfur‐, and oxygen‐containing nucleophiles. In this context, our group explored the ability of the G3-XantPhos palladium precatalyst[1] to promote the coupling of unprotected thiosugars with various halide partners at room temperature and in aquous medium. Some of these results will be present in this oral communication.[2]

Antivirulence approach aided by new potential antimicrobial substances

Messaoudi, S. et al. "2-Aminobiphenyl Palladacycles: the “Most Powerful” Precatalysts in C−C and C−heteroatom Cross-Couplings", ACS Catal. 2015, 5, 1386–1396

(a) Messaoudi, S. "Synthesis of Aryl-Thioglycopeptides Through Chemoselective Pd-Mediated Conjugation",Chem.Sci. 2018, 9, 8753-8759; (b) Messaoudi, S. " Efficient Buchwald–Hartwig–Migita Cross-Coupling for DNA Thioglycoconjugation", Chem. Eur. J. 2018, 24, 1795-1800; (c) Messaoudi, S. "Synthesis of (1 → 2)-S-Linked Saccharides and S-Linked Glycoconjugates via a Palladium-G3-XantPhos Precatalyst Catalysis", J. Org. Chem. 2017, 82, 6720–6728; (d) Bruneau, A.; Roche, M.; Hamze, A.; Brion, J.-D.; Alami, M.; Messaoudi, S. "Stereoretentive Palladium-Catalyzed Arylation, Alkenylation and Alkynylation of 1-Thiosugars and Thiols Using Aminobiphenyl Palladacycle Precatalyst at Room Temperature", Chem. Eur. J, 2015, 21, 8375 – 8379

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