Synthesis of Glycosyl Azides and Their Applications Using CuAAC Click Chemistry to Generate Bis- and Tris(triazolyl)glycosyl Derivatives

Autor(es)

Shamim, Anwar ^[1] ; Vasconcelos, Stanley N. S. ^[2] ; de Oliveira, Isadora Maria ^[1] ; Reis, Joel S. ^[2] ; Pimenta, Daniel C. ^[3] ; Zukerman-Schpector, Julio ^[4] ; Stefani, Helio A. ^[2]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim, Av Prof Lineu Prestes 748, BR-05508000 Sao Paulo, SP - Brazil

^[2] Univ Sao Paulo, Fac Ciencias Farmaceut, Av Prof Lineu Prestes 580, BR-0550800 Sao Paulo, SP - Brazil

^[3] Inst Butantan, Sao Paulo, SP - Brazil

^[4] Univ Fed Sao Carlos, Dept Quim, Sao Carlos, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: SYNTHESIS-STUTTGART; v. 49, n. 23, p. 5183-5196, DEC 2017.
• Citações Web of Science: 3

Resumo

2,3-Unsaturated C-(triazolyl) glycosyl acetates have been synthesized from 3,4,6-tri-O-acetyl-D-glucal using C-glycosylation and click chemistry and were then used in a palladium-catalyzed Tsuji-Trost type allylic azidation reaction to afford the corresponding regioisomeric glucal-azide derivatives. Copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions with these glucal-based allylic azides using CuI as the catalyst, led to the corresponding glucal-based bis(triazole) derivatives. Performing further functional group modification and another click (CuAAC) reaction with each of these bis(triazolyl) glycosyl derivatives afforded tris(triazolyl) glycosyl derivatives. Two libraries of regioisomeric bis(triazole) derivatives and a small library of regioisomeric tris(triazole) derivatives of glucal were then synthesized using different alkynes. (AU)

• Processo FAPESP: 12/00424-2 - Síntese de pequenas bibliotecas empregando organotrifluoroboratos de potássio em reações de Suzuki-Miyaura
• Beneficiário: Helio Alexandre Stefani
• Modalidade de apoio: Auxílio à Pesquisa - Temático