期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 17, 页码 9433-9438出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202014991
关键词
C-glycosylation; cross-coupling; glycosyl radicals; nucleoside analogues; photoredox
资金
- National Institute of Health [R01 GM-127778]
- Alfred P. Sloan Foundation [FG-2018-10354]
- Camille and Henry Dreyfus Foundation [TC-19-019]
- NSF MRI [1827902]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1827902] Funding Source: National Science Foundation
C-aryl glycosyl compounds offer improved in vivo stability compared to O- and N-glycoside analogues, making them attractive candidates for drug development and chemical biology studies. A new cross-coupling method has been developed for the preparation of C-aryl and heteroaryl glycosides, including nucleosides and 2-deoxysugars, from easily accessible glycosyl esters and bromoarenes, demonstrating the potential of this method in medicinal chemistry.
C-aryl glycosyl compounds offer better in vivo stability relative to O- and N-glycoside analogues. C-aryl glycosides are extensively investigated as drug candidates and applied to chemical biology studies. Previously, C-aryl glycosides were derived from lactones, glycals, glycosyl stannanes, and halides, via methods displaying various limitations with respect to the scope, functional-group compatibility, and practicality. Challenges remain in the synthesis of C-aryl nucleosides and 2-deoxysugars from easily accessible carbohydrate precursors. Herein, we report a cross-coupling method to prepare C-aryl and heteroaryl glycosides, including nucleosides and 2-deoxysugars, from glycosyl esters and bromoarenes. Activation of the carbohydrate substrates leverages dihydropyridine (DHP) as an activating group followed by decarboxylation to generate a glycosyl radical via C-O bond homolysis. This strategy represents a new means to activate alcohols as a cross-coupling partner. The convenient preparation of glycosyl esters and their stability exemplifies the potential of this method in medicinal chemistry.
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