Synthesis of 2'-([1,2,3]triazol-1-yl)-2'-deoxyadenosines.
A reliable and efficient protocol for the synthesis of 2 '-([1,2,3]triazol-1-yl)-2 '-deoxyadenosine derivatives from vidarabine is presented. Vidarabine was converted to 2'-azido-2'-deoxy-3',5-O-(tetraisopropyldisiloxane-1,3-diyl)-adenosine. This azide was used as the starting material for the Cu(I)-catalyzed parallel synthesis of 1,2,3-triazoles using a variety of alkynes. The reactions proceeded in good yield and gave almost exclusively the 1,4-disubstituted 1,2,3-triazoles.
O'Mahony
Gavin
G
Department of Chemistry, Medicinal Chemistry, Göteborg University, Göteborg, Sweden.
Svensson
Sara
S
Sundgren
Andreas
A
Grøtli
Morten
M
D000604:Amino Acyl-tRNA Synthetases / Q000037:antagonists & inhibitors; D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry; D014740:Vidarabine / Q000031:analogs & derivatives / Q000737:chemistry
D003839:Deoxyadenosines; D004791:Enzyme Inhibitors; D014230:Triazoles; D000604:Amino Acyl-tRNA Synthetases; D014740:Vidarabine