Dinucleotides of 4′-C-vinyl- and 5′-C-allylthymidine as substrates for ring-closing metathesis reactions |
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Authors: | Claus KirchhoffPoul Nielsen |
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Institution: | Nucleic Acid Center,††Nucleic Acid Center is funded by the Danish National Research Foundation for studies on nucleic acid chemical biology. Department of Chemistry, University of Southern Denmark, 5230 Odense M, Denmark |
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Abstract: | Thymidine derivatives containing a 4′-C-vinyl group or a 5′-C-allyl group are synthesized and used as building blocks for three different dinucleotides. These are evaluated as substrates for ring-closing metathesis cyclisations, and a protected 5′-C-allylthymidine homo-dimer is found to be the most reactive. A protected precursor for a conformationally restricted cyclic dinucleotide with a four carbon 5′-C to 5′-C connection is hereby efficiently obtained, whereas a corresponding three carbon 4′-C to 5′-C connection is obtained in a lower yield. |
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