Download PDF
Synfacts 2005(2): 0269-0269  
DOI: 10.1055/s-2005-916093
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Hybrid Solid/Solution-Phase Synthesis of Di- and Trinucleotides

Contributor(s): Yasuhiro Uozumi, Tomohiko Beppu
C. Dueymes, A. Schönberger, I. Adamoa, A.-E. Navarro, A. Meyer, M. Lange, J.-L. Imbach, F. Link, F. Morvan, J.-J. Vasseur*
University of Montpellier II, France
Further Information

Publication History

Publication Date:
25 October 2005 (online)

    Permissions and Reprints

Significance

Recyclable solid-supported reagents were applied to a new solution-phase phosphoramidite approach. Nucleoside-3′-O-phosphoramidite 1 was coupled with a nucleoside 2 by using polyvinyl pyridinium tosylate as an activator to give the desired phosphite triester 3. The resulting triester 3 was treated with polystyrene-bound trimethylammonium tetrathionate or periodiate to give the phosphotriester or thiono-phosphotriester analogue 4. Treatment of 4 with p-toluenesulfonic acid gave the 5′-OH nucleoside 5. Representative results are shown in the scheme (81-96% yields, 88-96% purity).