Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 1, Pages 374-381Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02768
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Funding
- National Institute of General Medical Sciences [GM111835, GM120673]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [U01GM120673, R01GM111835] Funding Source: NIH RePORTER
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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 to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.
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