Oxidative Activation of C-S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides.
Accepted version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Kitowski, Annabel
Jiménez-Moreno, Ester
Salvadó, Míriam
Mestre, Jordi https://orcid.org/0000-0002-4279-350X
Castillón, Sergio
Abstract
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.
Description
Keywords
3402 Inorganic Chemistry, 3404 Medicinal and Biomolecular Chemistry, 3405 Organic Chemistry, 34 Chemical Sciences
Journal Title
Org Lett
Conference Name
Journal ISSN
1523-7060
1523-7052
1523-7052
Volume Title
19
Publisher
American Chemical Society (ACS)
Publisher DOI
Sponsorship
European Commission (626890)
Engineering and Physical Sciences Research Council (EP/M003647/1)
The Royal Society (uf110046)
European Research Council (676832)
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (701473)
European Commission (EC) (852985)
Engineering and Physical Sciences Research Council (EP/M003647/1)
The Royal Society (uf110046)
European Research Council (676832)
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (701473)
European Commission (EC) (852985)