Synthesis of oligoribonucleotides by the H-phosphonate method using base-labile 2'-O-protecting groups. II. Some aspects of use of 2'-O-benzoyl and anizoyl protecting groups

E. Rozners, A . Rekis, V. Kumpins, E. Bizdena

Riga Polytechnical Institute

Abstract: The N-acyl, 5'-O-trityl (MeOTr, (MeO)₂Tr, Me₃Tr), 2'-O-benzoyl (and anisoyl) nucleosides were prepared by selective aroylation of N,5'-protected nucleosides. By means of the reverse-phase microcolumn liquid chromatography it was shown that the rate of the aroyl 2'→3'-isomerisation is lower in case of 2'-anisoylnucleosides and depends on structure of the 5'-O-protecting group. The prepared synthons were used for the manual H-phosphonate solid-phase synthesis of oligoribonucleotides (6–10-mers).

Russian Journal of Bioorganic Chemistry 1990, 16 (11):1531-1536

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