Abstract
3′-O-Methylthiomethyl derivatives of ribonucleosides were synthesized from the selectively protected nucleosides by the action of a dimethyl sulfide-benzoyl peroxide mixture in acetonitrile or a dimethyl sulfoxide-acetic anhydride-acetic acid mixture.
Similar content being viewed by others
References
Pechenov, A.E., Zavgorodny, S.G., Shvets, V.I., and Miroshnikov, A.I.,Bioorg. Khim., 2000, vol. 26, pp. 362–368.
Matteucci, M.,Tetrahedron Lett., 1990, vol. 31, pp. 2385–2388.
Veeneman, G.H., van der Marel, G.A., van den Elst, H., and van Boom, J.H.,Rec. Trav. Chim. Pays-Bas, 1990, vol. 109, pp. 449–451.
Veeneman, G.H., van der Marel, G.A., van den Elst, H., and van Boom, J.H.,Tetrahedron, 1991, vol. 47, pp. 1547–1562.
Oivanen, M., Viinamäki, T., Zavgorodny, S., Poliansky, M., Azhayev, A., van Aerschot, A., Herdewijn, P., and Lönnberg, H.,Collect. Czech. Chem. Commun., 1990, vol. 55, pp. 17–20.
Zavgorodny, S., Poliansky, M., Kriukov, V., Oksman, P., Hakala, H., Lönnberg, H., van Aerschot, A., Herdewijn, P., and Azhayev, A.,Nucleic Acids Res., 1991, vol. 19, p. 295.
Zavgorodny, S., Poliansky, M., Besidsky, E., Kriukov, V., Sanin, A., Pokrovskaya, M., Gurskaya, G., Lönnberg, H., and Azhayev, A.,Tetrahedron Lett., 1991, vol. 32, pp. 7593–7596.
Hsu, L.-Y., Wise, D.S., Kucera, L.S., Drach, J.C., and Townsend, L.B.,J. Org. Chem., 1992, vol. 57, pp. 3354–3358.
Jones, R.J., Lin, K.-Y., Milligan, J., Wadwani, S., and Matteucci, M.,J. Org. Chem., 1993, vol. 58, pp. 2983–2991.
Lin, K.-Y., Pudlo, J.S., Jones, R.J., Bishofberger, N., Matteucci, M.D., and Froehler, B.C.,Biomed. Chem. Lett., 1994, vol. 4, pp. 1061–1064.
Ducharme, Y. and Harrison, K.A.,Tetrahedron Lett., 1995, vol. 36, pp. 6643–6646.
Karpeisky, A., Gonzalez, C., Burgin, A.B., Usman, N., and Beigelman, L.,Nucleosides Nucleotides, 1997, vol. 16, pp. 955–958.
He, G.-X. and Bishofberger, N.,Tetrahedron Lett., 1997, vol. 38, pp. 945–948.
Hansske, F., Madej, D., and Robins, M.J.,Tetrahedron, 1984, vol. 40, pp. 125–135.
Gavagnin, M. and Sodano, G.,Nucleosides Nucleotides, 1989, vol. 8, pp. 1319–1324.
Medina, J.C., Salomon, M., and Kyler, K.S.,Tetrahedron Lett., 1988, vol. 29, pp. 3773–3776.
Hakimelahi, G.H., Proba, Z.A., and Ogilvie, K.K.,Can. J. Chem., 1982, vol. 60, pp. 1106–1113.
Ogilvie, K.K., Beaucage, S.L., Schifman, N.L., Theriault, N.Y., and Sadana, K.L.,Can. J. Chem., 1978, vol. 56, pp. 2768–2780.
Van Boom, J.H. and Wreesmann, C.T.J.,Oligonucleotide Synthesis: A Practical Approach, Gait, M.J., Ed., Oxford: IRL, 1984, pp. 153–182.
Eckstein, F. and Cramer, F.,Chem. Ber., 1965, vol. 98, pp. 995–997.
Griffin, B.E., Jarman, M., Reese, C.B., and Sulston, J.E.,Tetrahedron, 1967, vol. 23, pp. 2301–2313.
Fromageot, H.P.M., Jarman, M., Reese, C.B., and Sulston, J.E.,Tetrahedron, 1967, vol. 23, pp. 2315–2331.
Author information
Authors and Affiliations
Corresponding author
Additional information
For communication I, see [1].
Rights and permissions
About this article
Cite this article
Pechenov, A.E., Zavgorodny, S.G., Shvets, V.I. et al. TheS,X-acetals in nucleoside chemistry: II. The synthesis of 3′-O-methylthiomethylribonucleosides. Russ J Bioorg Chem 26, 407–413 (2000). https://doi.org/10.1007/BF02758669
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02758669