title: Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-O-acetyl-D-glucal.
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-O-acetyl-D-glucal-derived mesylate. This mesylate was obtained from 3,4,6-tri-O-acetyl-D-glucal through C-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.
authors.affiliation: Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil.
authors.forename: Anwar
authors.initials: A
authors.lastname: Shamim
authors.forename: Frederico B
authors.initials: FB
authors.lastname: Souza
authors.forename: Gustavo H G
authors.initials: GH
authors.lastname: Trossini
authors.forename: Fernando M
authors.initials: FM
authors.lastname: Gatti
authors.forename: Hélio A
authors.initials: HA
authors.lastname: Stefani
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry; D006031:Glycosylation; D007454:Iodides / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D007454:Iodides; D014230:Triazoles; C043334:3,4,6-tri-O-acetylglucal; D003300:Copper; C073870:cuprous iodide; D003847:Deoxyglucose