C2-symmetric macrocyclic carbohydrate/amino acid hybrids through copper(I)-catalyzed formation of 1,2,3-triazoles.
An efficient method was developed for the preparation of macrocyclic carbohydrate/amino acid hybrids by macrocyclization with copper(I)-catalyzed 1,2,3-triazole formation. Methyl 2-amino-6-azido-3,4-di-O-benzoyl-2,6-dideoxy-beta-D-glucopyranoside was prepared and coupled to two different N-propiolyl dipeptides (propiolyl-Tyr-Tyr-OH and propiolyl-Arg(Mtr)-Tyr-OH) to obtain bifunctional molecules carrying one azido group and one terminal alkyne. These bifunctional molecules were cyclodimerized using Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes to form macrocycles containing two 1,2,3-triazoles. Various cyclization methods were evaluated, and the most efficient conditions were found to be CuI and N,N-diisopropylethylamine in CH3CN.
Billing
Johan F
JF
Organic Chemistry, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
Nilsson
Ulf J
UJ
D000596:Amino Acids / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D004151:Dipeptides / Q000138:chemical synthesis*; D008968:Molecular Conformation; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis*
D000596:Amino Acids; D002241:Carbohydrates; D004151:Dipeptides; D014230:Triazoles; D003300:Copper