Skip to main content
SpringerLink
Log in

Acyclic analogs of nucleosides. Synthesis of chiral 1,5-dihydroxy-4-methyl-3-oxapent-2-yl derivatives of uracil

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A convenient method has been developed for the synthesis of optically active 1-[1,5-dihydroxy-4-(R)-methyl-3-oxapent-2(R and S)-yl]uracils. 5′-Deoxyuridine is obtained from 2′,3′-O-isopropylideneuridine, and its periodate oxidation followed by reduction with sodium tetrahydroborate leads to the desired 4(R), 2(R)-isomer. The acetonide of α-uridine is converted into the 4(R),2(S)-isomer analogously.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature Cited

  1. J. L. Kelley and L. Beauchamp, Annu. Rep. Med. Chem., 18, 139 (1983).

    Google Scholar 

  2. R. L. Remy and J. A. Secrist, Nucleosides Nucleotides, 4, 411 (1985).

    Google Scholar 

  3. A. M. Kritsyn, S. W. Mikhailov, A. Yu. Misharin, N. Sh. Padyukova, and V. L. Florent'ev, Bioorg. Khim., 2, 1338 (1976).

    Google Scholar 

  4. S. N. Mikhailov, Bioorg. Khim., 4, 639 (1978).

    Google Scholar 

  5. M. MacCoss, A. Chen, and R. Tolman, Tetrahedron Lett., 26, 4287 (1985).

    Google Scholar 

  6. M. Ya. Karpeiskii, V. N. Senchenko, G. I. Yakovlev, and E. Yu. Kolbanovskaya, Bioorg. Khim., 8, 386 (1982).

    Google Scholar 

  7. K. K. Ogilvie, N. Nguyen-ba, M. P. Gillen, B. K. Radatus, U. O. Cheriyan, H. R. Hanna, K. O. Smith, and K. S. Galloway, Can. J. Chem., 62, 241 (1984).

    Google Scholar 

  8. J. Tomacz, in: Nucleic Acids Chemistry. Improved and New Synthetic Procedures, (ed. L. B. Townsend and R. G. Tipson), Wiley-Interscience, New York, Part 2 (1978), p. 765.

    Google Scholar 

  9. S. N. Mikhailov, Bioorg. Khim., 10, 940 (1984).

    Google Scholar 

  10. J. P. H. Verheyden and J. G. Moffatt, J. Org. Chem., 37, 2289 (1972).

    Google Scholar 

  11. H. G. Kuivila, Synthesis, No. 10, 499 (1970).

    Google Scholar 

  12. T. W. Green, Protective Groups in Organic Synthesis, Wiley-Interscience, New York (1981), p. 76.

    Google Scholar 

  13. Y. Wang, H. P. C. Hogenkamp, R. A. Long, G. P. Ravankar, and R. K. Robins, Carbohydr. Res., 59, 449 (1977).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Molecular Biology, USSR Academy of Sciences, Moscow

    S. N. Mikhailov & N. B. Grishko

Authors
  1. S. N. Mikhailov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. B. Grishko
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 91–94, January, 1988.

The authors thank Prof. M. Ya. Karpeiskii for constant interest in this work.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mikhailov, S.N., Grishko, N.B. Acyclic analogs of nucleosides. Synthesis of chiral 1,5-dihydroxy-4-methyl-3-oxapent-2-yl derivatives of uracil. Chem Heterocycl Compd 24, 75–78 (1988). https://doi.org/10.1007/BF00475574

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00475574

Keywords

Search

Navigation