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

Autor(es)

Goncalves, Renan. O. ; Oliveira, Pedro H. R. ; de Jesus, Iva S. ; Debia, Natali P. ; Ludtke, Diogo S. ; Paixao, Marcio W.

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 21, n. 27, p. 5-pg., 2023-06-14.

Resumo

C-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 & beta;-alanine analog. (AU)

• Processo FAPESP: 21/06099-5 - Desenvolvimento de novas metodologias fotoquímicas para síntese de pequenas moléculas e modificações de biomoléculas
• Beneficiário: Márcio Weber Paixão
• Modalidade de apoio: Auxílio à Pesquisa - Regular