Oxidative Activation of C-S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides.
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Authors
Kitowski, Annabel
Jiménez-Moreno, Ester
Salvadó, Míriam
Castillón, Sergio
Lopes Bernardes, Goncalo
Publication Date
2017-10Journal Title
Organic letters
ISSN
1523-7060
Publisher
American Chemical Society
Volume
19
Issue
19
Pages
5490-5493
Language
eng
Type
Article
This Version
AM
Physical Medium
Print-Electronic
Metadata
Show full item recordCitation
Kitowski, A., Jiménez-Moreno, E., Salvadó, M., Mestre, J., Castillón, S., Jiménez-Osés, G., Boutureira, O., & et al. (2017). Oxidative Activation of C-S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides.. Organic letters, 19 (19), 5490-5493. https://doi.org/10.1021/acs.orglett.7b02886
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 C-2 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.
Sponsorship
European Commission (626890)
EPSRC (EP/M003647/1)
Royal Society (uf110046)
European Commission Horizon 2020 (H2020) ERC (676832)
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (701473)
Identifiers
External DOI: https://doi.org/10.1021/acs.orglett.7b02886
This record's URL: https://www.repository.cam.ac.uk/handle/1810/276026
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