Chemoenzymatic Synthesis of 3a2-Deoxy-3a2-(4-Substituted-Triazol-1-YL)-5-Methyluridine

• Published in: Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2013-01, Vol.32 (12), p.646-659
• Main Authors: Arya, Anu, Mathur, Divya, Tyagi, Abhilash, Kumar, Rajesh, Kumar, Vinod, Olsen, Carl, Saxena, Rajendra, Prasad, Ashok
• Format: Article
• Language: English
• ISSN: 1525-7770; 1532-2335
• DOI: 10.1080/15257770.2013.847957

An efficient protocol has been developed for the synthesis of a small library of 3a2-deoxy-3a2-(4-substituted-triazol-1-yl)-5-methyluridine using Cu(I)-catalyzed HuisgenaSharplessaMeldal 1,3-dipolar cycloaddition reaction of 3a2-azido-3a2-deoxy-5-methyluridine with different alkynes under optimized condition in an overall yields of 76%a92%. Here, the azido precursor compound, i.e., 3a2-azido-3a2-deoxy-5-methyluridine was chemoenzymatically synthesized from D-xylose in good yield. Some of the alkynes used in cycloaddition reaction were synthesized by the reaction of hydroxycoumarins or naphthols with propargyl bromide in acetone using K2CO3in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, 1H-, 13C NMR spectra, and high-resolution mass spectra) data analysis.