Synthesis of non-anomeric C -glycosyl pyrazolidinone derivatives via visible-light photoredox catalysis

-Glycosyl compounds have gained considerable attention over the last few decades due to their high chemical stability and promising applications in drug discovery. Herein we disclose an operationally simple, metal-free, photocatalytic approach for the glycosylation of azomethine imines using 4-glyco...

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Veröffentlicht in:Organic & biomolecular chemistry 2023-07, Vol.21 (27), p.5516-5520
Hauptverfasser: Gonçalves, Renan O, Oliveira, Pedro H R, de Jesus, Iva S, Debia, Natalí P, Lüdtke, Diogo S, Paixão, Márcio W
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Sprache:eng
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Zusammenfassung:-Glycosyl compounds have gained considerable attention over the last few decades due to their high chemical stability and promising applications in drug discovery. Herein we disclose an operationally simple, metal-free, photocatalytic approach for the glycosylation of azomethine imines using 4-glycosyl-1,4-dihydropyridines (DHPs) as radical precursors. The protocol features mild reaction conditions, scalability, broad substrate scope, and good functional group tolerance. Moreover, the resulting pyrazolidinone moiety can be easily deprotected, acylated or reduced into a glycosyl β-alanine analog.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00775h