Download PDF
Synfacts 2006(9): 0965-0965  
DOI: 10.1055/s-2006-949247
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted ‘Click’ Chemistry on Solid Support

Contributor(s): Yasuhiro Uozumi, Maki Minakawa
C. Bouillon, A. Meyer, S. Vidal, A. Jochum, Y. Chevolot, J.-P. Cloarec, J.-P. Praly, J.-J. Vasseur, F. Morvan*
Université Montpellier II, Université Claude Bernard Lyon 1 and École Centrale de Lyon, France
Further Information

Publication History

Publication Date:
23 August 2006 (online)

    Permissions and Reprints

Significance

Microwave-assisted efficient Cu(I)-catalyzed ‘click’ coupling on solid support is described. The 1,3-dipolar cycloaddition of alkyne-functionalized oligonucleotide 1 (0.5 mmol) and galactosyl azidederivative 2 (5 mmol, 3.3 mol equiv of alkyne) was performed on solid support in the presence of CuSO4 (0.2 mmol) and sodium ascorbate (1 mmol) in MeOH-H2O (1:1, 200 ml) with microwave irradiation (100 W, at 60 °C for 20 min) to give the solid-supported protected trigalactosylated oligonucleotide 3 (100% conversion). Cleavage of the solid support and the protecting acetyl groups was accomplished in one step by treatment with aqueous ammonia to give the fully deprotected trigalactosylated T12 4 in solution.