Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-O-acetyl-D-glucal

Autor(es)

Shamim, Anwar ^[1] ; Souza, Frederico B. ^[2] ; Trossini, Gustavo H. G. ^[2] ; Gatti, Fernando M. ^[2] ; Stefani, Helio A. ^[2]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim, Sao Paulo, SP - Brazil

^[2] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: MOLECULAR DIVERSITY; v. 19, n. 3, p. 423-434, AUG 2015.
• Citações Web of Science: 5

Resumo

We have developed an efficient, CuI-catalyzed, microwave-assisted method for the synthesis of bis-1,2,3-triazole derivatives starting from a 3,4,6-tri--acetyl-d-glucal-derived mesylate. This mesylate was obtained from 3,4,6-tri--acetyl-d-glucal through -glycosidation, deprotection of acetate groups to alcohols, and selective mesylation of the primary alcohol. This mesylate moiety was then converted to an azide through a microwave-assisted method with good yield. The azide, once synthesized, was then treated with different terminal alkynes in the presence of CuI to synthesize various bis-triazoles in high yields and short reaction times. (AU)

• Processo FAPESP: 13/20553-4 - Síntese e funcionalização de iodeto de sulfóxidos vinílicos
• Beneficiário: Frederico Bernardes de Souza
• Modalidade de apoio: Bolsas no Brasil - Doutorado Direto
• 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