Synthesis of 2 '- or 3 '-o-(4-methoxybenzyl)nucleosides and its application in the 3 '-terminal nonanucleotide sequence of rous sarcoma virus 35S RNA synthesis

Abstract

2'- or 3'-O-(4-Methoxybenzyl)nucleoside derivatives were synthesized by treatment of uridine, N 4-benzoylcytidine, N 6-benzoyladenosine, and N 2-benzoylguanosine with 4-methoxy-phenyldiazomethane. The separation of 2'- or 3'-isomers became possible on a silica gel column chromatography by using N-acylated nucleosides and these compounds could be used as useful starting materials for the synthesis of oligoribonucleotides by the phosphotriester method. The trimer blocks, U-U-Cp, A-C-Cp, and A-C-A were synthesized by the rapid method. The 3'-terminal nonanucleotide, U-U-C-A-C-C-A-C-A, of Rous Sarcoma Virus 35S RNA was obtained by the block condensation of trimers.