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

Author(s)

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

Affiliation

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

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

• Document type: Journal article
• Source: MOLECULAR DIVERSITY; v. 19, n. 3, p. 423-434, AUG 2015.
• Web of Science Citations: 5

Abstract

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)

• FAPESP's process: 13/20553-4 - Synthesis and functionalization of vinyl iodide sulfoxides
• Grantee: Frederico Bernardes de Souza
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
• Grantee: Helio Alexandre Stefani
• Support Opportunities: Research Projects - Thematic Grants