The Ring Opening of Cyclopentene Oxides by Pyrimidines and Purines as a Pathway to Carbocyclic Nucleoside Analogues

Article abstract of DOI:10.1007/BF00807105

Various carbocyclic nucleosides with xylo-configuration have been synthesized using ring opening of 5-O-acetyl-1,2-anhydro-3-O-benzylcarba-α-DL-xylo-pentofuranose (6) by thymine, uracil, 4-N-benzoylcytosine, adenine, 6-N-benzoyladenine, and 2-amino-6-chloropurine in alkaline medium. For this purpose, the use of triethylaluminum is introduced into carbanucleoside chemistry. The new method proved to be superior over the application of sodium hydride and potassium or caesium carbonate.