Microwave-enhanced ionothermal CuAAC for the synthesis of glycoclusters on a calix[4]arene platform.
A tetra-azido calix[4]arene derivative was allowed to react with ethynyl tetra- O-benzyl- C-galactoside in the presence of CuI and i-Pr 2EtN in three different ionic liquids, that is, [C 8dabco][N(CN) 2], [C 8dabco][Br], and Ammoeng 110. Reactions were performed at 80 degrees C by thermal and MW dielectric heating. In all cases, multiple cycloadditions took place to give a triazole-linked tetra- C-galactosyl-calix[4]arene in up to 90% yield. The [C 8dabco][N(CN) 2] ionic liquid was also used to perform the multiclick reactions with propargyl O-lactoside and S-sialoside.
Vecchi
Alessandra
A
Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, 44100 Ferrara, Italy.
Melai
Bernardo
B
Marra
Alberto
A
Chiappe
Cinzia
C
Dondoni
Alessandro
A
D047250:Calixarenes / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D005697:Galactosides / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis*; D008872:Microwaves; D009942:Organometallic Compounds / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry
D005697:Galactosides; D006001:Glycoconjugates; D009942:Organometallic Compounds; D010636:Phenols; D014230:Triazoles; C121325:calix(4)arene; D047250:Calixarenes; D003300:Copper