Organic Letters
Organic Letters
5 years ago

Oxidative Activation of C–S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides

Oxidative Activation of C–S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides
Gonçalo J. L. Bernardes, Míriam Salvadó, Omar Boutureira, Jordi Mestre, Annabel Kitowski, Gonzalo Jiménez-Osés, Ester Jiménez-Moreno, Sergio Castillón
A method for the selective activation of thioglycosides that uses the N+-thiophilic reagent O-mesitylenesulfonylhydroxylamine (MSH) as a promoter is presented. The reaction proceeds via anomeric mesitylensulfonate intermediates, which could be isolated and fully characterized by placing a fluorine atom at the C2 position. In the presence of a soft Lewis acid, glycosylation reaction proceeds at ambient temperature with good yields. It is further demonstrated that it is possible to orthogonally activate S-ethyl in the presence of S-phenyl donors, enabling the design of sequential glycosylation strategies.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02886

DOI: 10.1021/acs.orglett.7b02886

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