Synthesis of the bicyclo-[4.3.0]-thymidyl-nucleoside via pd(II)-mediated ring expansion chemistry.
A variety of modified nucleosides to improve antisense oligodeoxynucleotide properties such as target affinity, nuclease resistance, and pharmacokinetics were developed in the last two decades. In the context of conformational restriction we present here the synthesis of the [4.3.0]-bicyclo-DNA thymine monomer via Pd(II)-mediated ring expansion of an intermediate of the tricyclo-DNA synthesis.
Stauffiger
Andrea
A
Department of Chemistry and Biochemistry, University of Bern, Bern, Switzerland. stauffiger@ioc.unible.ch
Leumann
Christian J
CJ
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry*; D013941:Thymine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C526389:2',6'-dihydroxy-8'-(thymin-1-yl)-9'-oxabicyclo(4.3.0)nonane; D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D010165:Palladium; D013941:Thymine