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Stereoselective Synthesis of Carbon-Sulfur-Bridged Glycomimetics by Photoinitiated Thiol-Ene Coupling Reactions

1
Department of Pharmaceutical Chemistry University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
2
Department of Organic Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
3
Doctoral School of Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(2), 573; https://doi.org/10.3390/ijms21020573
Received: 20 December 2019 / Revised: 13 January 2020 / Accepted: 15 January 2020 / Published: 16 January 2020
Oligosaccharides and glycoconjugates are abundant in all living organisms, taking part in a multitude of biological processes. The application of natural O-glycosides in biological studies and drug development is limited by their sensitivity to enzymatic hydrolysis. This issue made it necessary to design hydrolytically stable carbohydrate mimetics, where sulfur, carbon, or longer interglycosidic connections comprising two or three atoms replace the glycosidic oxygen. However, the formation of the interglycosidic linkages between the sugar residues in high diastereoslectivity poses a major challenge. Here, we report on stereoselective synthesis of carbon-sulfur-bridged disaccharide mimetics by the free radical addition of carbohydrate thiols onto the exo-cyclic double bond of unsaturated sugars. A systematic study on UV-light initiated radical mediated hydrothiolation reactions of enoses bearing an exocyclic double bond at C1, C2, C3, C4, C5, and C6 positions of the pyranosyl ring with various sugar thiols was performed. The effect of temperature and structural variations of the alkenes and thiols on the efficacy and stereoselectivity of the reactions was systematically studied and optimized. The reactions proceeded with high efficacy and, in most cases, with complete diastereoselectivity producing a broad array of disaccharide mimetics coupling through an equatorially oriented methylensulfide bridge. View Full-Text
Keywords: carbohydrate; disaccharide; glycomimetic; thioglycoside; C-glycoside; photochemical addition; thiyl radical; diastereoselective synthesis carbohydrate; disaccharide; glycomimetic; thioglycoside; C-glycoside; photochemical addition; thiyl radical; diastereoselective synthesis
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Csávás, M.; Eszenyi, D.; Mező, E.; Lázár, L.; Debreczeni, N.; Tóth, M.; Somsák, L.; Borbás, A. Stereoselective Synthesis of Carbon-Sulfur-Bridged Glycomimetics by Photoinitiated Thiol-Ene Coupling Reactions. Int. J. Mol. Sci. 2020, 21, 573.

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