Synthesis of 3-Adenyl- and 3-Thyminylcyclobutane-1,1-dimethanols and Their Homo-octameric Phosphodiesters

Starting from 3-(benzyloxy)cyclobutane-1,1-dimethanol, 3-thyminyl- and 3-adenylcyclobutane-1,1-dimethanol were synthesized by direct introduction of the heterocycles (Scheme 1). The mono-O-substituted methoxytrityl derivatives were separately converted to octameric phosphodiesters on an aminomethyl-polystyrene carrier by the phosphotriester method. These oligomers of carba-nucleosides were prepared in order to study their annealing behaviour towards ribo- and deoxyribo-nucleic acids as well as their potential for homologous hybridization.