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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

M. Richard, M. Richard, Claude Didierjean, Claude Didierjean, Yves Chapleur, Yves Chapleur, N. Pellegrini-Moïse, N. Pellegrini-Moïse
Published 2015 · Chemistry

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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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