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OFox imidates as versatile glycosyl donors for chemical glycosylation.

ABSTRACT: Previously we communicated 3,3-difluoroxindole (HOFox) - mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study with the main focus on the synthesis of various OFox imidates and their investigation as glycosyl donors for chemical 1,2-cis and 1,2-trans glycosylation.

SUBMITTER: Nigudkar SS

PROVIDER: S-EPMC5499515 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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OFox imidates as versatile glycosyl donors for chemical glycosylation.

Nigudkar Swati S SS Wang Tinghua T Pistorio Salvatore G SG Yasomanee Jagodige P JP Stine Keith J KJ Demchenko Alexei V AV

Organic & biomolecular chemistry 20170101 2

Previously we communicated 3,3-difluoroxindole (HOFox) - mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study with the main focus on the synthesis of various OFox imidates and their investigation as glycosyl donors for chemical 1,2-cis and 1,2-trans glycosylation ...[more]

PMID: 27808325

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