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Base- and Radical-Mediated Regio- and Stereoselective Additions of Thiols, Thio-Sugars, and Thiol-Containing Peptides to Trisubstituted Activated exo -Glycals

Abstract : A study was performed for the coupling of thiols, thio-sugars, and thiol-containing amino acids and peptides with trisubstituted activated anomeric sugar olefins under basic and radical conditions. The hydrothiolation reaction took place in a regio- and stereospecific manner and occurred at the anomeric center and mainly from an approach to the less crowded face, that is, opposite to the O-4 protecting group. Furano- and pyranoglycosylidenes were valuable substrates for the base-mediated coupling with aromatic and primary thiols, which included 6-thio-sugars, cysteine derivatives, and glutathione. The success of the radical-mediated method depended on the thiol partners as well as the nature of the sugar olefins. Neither of the conditions required the protection of the sugar or the cysteine derivatives.
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Submitted on : Monday, March 27, 2017 - 10:36:08 AM
Last modification on : Friday, February 26, 2021 - 3:24:02 PM

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Mylène Richard, Claude Didierjean, Yves Chapleur, Nadia Pellegrini-Moïse. Base- and Radical-Mediated Regio- and Stereoselective Additions of Thiols, Thio-Sugars, and Thiol-Containing Peptides to Trisubstituted Activated exo -Glycals. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (12), pp.2632 - 2645. ⟨10.1002/ejoc.201500130⟩. ⟨hal-01495995⟩

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