C2-Symmetric Macrocyclic Carbohydrate/Amino Acid Hybrids through Copper(I)-Catalyzed Formation of 1,2,3-Triazoles

Summary, in English

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--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.

• Author: Johan Billing; Ulf Nilsson
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2005
• Language: English
• Pages: 4847-4850
• Publication/Series: Journal of Organic Chemistry
• Volume: 70
• Issue: 12
• Links: http://dx.doi.org/10.1021/jo050585l
• Document type: Journal article
• Publisher: The American Chemical Society (ACS)
• Topic: Organic Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 1520-6904