Abstract
The chlorination of 2-halomethyltetrahydrofurans and acyl derivatives of tetrahydrofuryl alcohol wasstudied; mixtures of 2,5- and 2,2-disubstituted tetrahydrofurans are formed as a result of the reaction. 2,4-Bis(trimethylsilyl) derivatives of uracil, 5-substituted uracils, and cytosine are alkylated by the resulting mixtures of α-chloro ethers without separation, and mixtures of cis and transisomers of 1-(5-substituted-2-tetrahydrofuryl) and 1-(2-substituted-2-tetrahydrofuryl) derivatives of uracil, 5-substituted uracils, and cytosine are obtained. The reaction products were identified onthe basis of their PMR spectra.
Similar content being viewed by others
Literature cited
L. T. Kaulinya, R. A. Zhuk, and M. Yu. Lidak, Khim. Geterotsikl. Soedin., No. 8, 1094 (1981).
A. M. Doering, M. Jansen, and S. S. Cohen, J. Bacteriol., 92, 565 (1966).
M. R. Atkinson, M. P. Deutscher, A. Kornberg, A. F. Russell, and J. G. Moffatt, Biochemistry, 8, 4897 (1969).
F. Sanger, S. Nicklen, and A. R. Coulson, Proc. Natl. Acad. Sci. USA, 74, 5463 (1977).
W. Plunkett and S. S. Cohen, Cancer Res., 35, 1547 (1975).
P. Langen, G. Etzold, and G. Kowollik, Acta Biol. Med. Germ., 28, K5-K10 (1972).
A. Gangjee, H. P. C. Hogenkamp, and J. M. Kitzen, J. Pharm. Sci., 67, 121 (1978).
H. Gross, Chem. Ber., 95, 83 (1962).
M. Kratokhvil and I. Gort, Collect. Czech. Chem. Commun., 27, 52 (1962).
R. A. Zhuk, A. É. Berzinya, V. N. Silinya, É. É. Liepin'sh, and S. A. Giller, Khim. Geterotsikl. Soedin., No. 2, 166 (1979).
E. P. Vechirko, N. V. Kondratenko, L. M. Yagupol'skii, É. É. Liepin'sh, and E. G. Shpaer, Zh. Org. Khim., 17, 186 (1981).
S. A. Giller, M. Yu. Lidak, R. A. Zhuk, A. É. Berzinya, K. Ya. Pets, I. N. Getsova, and E. I. Bruk, Khirn. Geterotsikl. Soedin., No. 2, 375 (1969).
C. G. Kruse, H. P. M. de Leeuw, and A. van der Gen, J. Chem. Soc., Perkin II, 827 (1979).
J. Zemlicka and J. P. Horwitz, J. Am. Chem. Soc., 97, 4089 (1975).
G. M. Tener, J. Am. Chem. Soc., 83, 159 (1961).
M. Joshikawa, T. Kato, and T. Takenishi, Tetrahedron Lett., 5056 (1967).
M. Joshikawa, T. Kato, and T. Takenishi, Bull. Chem. Soc. Jpn., 42, 3505 (1969).
A. L. Ponomarev, Syntheses and Reactions of Furan Substances [in Russian], Moscow (1960), p. 205.
L. Brookes and H. Snyder, Organic Syntheses [Russian translation], Vol.3, Inostr. Lit., Moscow (1952), p. 374.
Author information
Authors and Affiliations
Additional information
See [1] for Communication 15.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 101–110, January, 1982.
Rights and permissions
About this article
Cite this article
Kaulinya, L.T., Liepin'sh, É.É., Lidak, M.Y. et al. Analogs of pyrimidine nucleosides. 16. Racemic 2′,3′-dideoxynucleosides and their derivatives. Chem Heterocycl Compd 18, 85–93 (1982). https://doi.org/10.1007/BF00513297
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00513297