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Regenerative glycosylation under nucleophilic catalysis.

ABSTRACT: This article describes 3,3-difluoroxindole (HOFox)-mediated glycosylation. The uniqueness of this approach is that both the in situ synthesis of 3,3-difluoro-3H-indol-2-yl (OFox) glycosyl donors and activation thereof can be conducted in a regenerative fashion as is a typical reaction performed under nucleophilic catalysis. Only a catalytic amount of the OFox imidate donor and a Lewis acid activator are present in the reaction medium. The OFox imidate donor is constantly regenerated upon its consumption until glycosyl acceptor has reacted.

SUBMITTER: Nigudkar SS

PROVIDER: S-EPMC3933924 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Regenerative glycosylation under nucleophilic catalysis.

Nigudkar Swati S SS Stine Keith J KJ Demchenko Alexei V AV

Journal of the American Chemical Society 20140109 3

This article describes 3,3-difluoroxindole (HOFox)-mediated glycosylation. The uniqueness of this approach is that both the in situ synthesis of 3,3-difluoro-3H-indol-2-yl (OFox) glycosyl donors and activation thereof can be conducted in a regenerative fashion as is a typical reaction performed under nucleophilic catalysis. Only a catalytic amount of the OFox imidate donor and a Lewis acid activator are present in the reaction medium. The OFox imidate donor is constantly regenerated upon its con ...[more]

PMID: 24393099

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