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Oxidative activation of C-S bonds with an electropositive nitrogen promoter enables orthogonal glycosylation of alkyl over phenyl thioglycosides

Kitowski, A and Jiménez-Moreno, E and Salvadó, M and Mestre, J and Castillón, S and Jiménez-Osés, G and Boutureira, O and Bernardes, GJL (2017) Oxidative activation of C-S bonds with an electropositive nitrogen promoter enables orthogonal glycosylation of alkyl over phenyl thioglycosides. Organic Letters, 19. pp. 5490-5493. ISSN 1523-7060

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Abstract

A method for the selective activation of thioglycosides that uses the N+-thiophilic reagent Omesitylenesulfonylhydroxylamine (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.

Item Type: Article
Subjects: UNSPECIFIED
Divisions: UNSPECIFIED
Depositing User: Cron Job
Date Deposited: 25 Jun 2019 02:49
Last Modified: 15 Apr 2021 06:04
DOI: 10.1021/acs.orglett.7b02886