Skip to main content
Log in

New method for the synthesis of 2-acylamino glycals

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A new method for the synthesis of 2-acylamino glycal derivatives was developed, which helps to considerably simplify the preparation and increase the yield of the target compounds. For the first time, a method for the preparation of 2-amino-D-glucal derivative containing a 2,2,2-trichloroethoxycarbonyl N-protecting group was proposed.

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

Access this article

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

Instant access to the full article PDF.

References

  1. J. F. Robyt, in Glycoscience: Chemistry and Chemical Biology, Eds B. O. Fraser-Reid, K. Tatsuta, J. Thiem, Springer Berlin Heidelberg, Berlin, Heidelberg, 2001, p. 76; DOI: https://doi.org/10.1007/978-3-642-56874-9_4.

  2. Yu. E. Tsvetkov, O. N. Yudina, N. E. Nifantiev, Russ. Chem. Rev., 2021, 90, 171; DOI: https://doi.org/10.1070/RCR4974.

    Article  CAS  Google Scholar 

  3. A. A. Chinarev, M. A. Sablina, R. A. Kunetskiy, N. V. Shilova, S. V. Polyakova, A. S. Paramonov, J. Sahab, N. V. Bovin, Mendeleev Commun., 2021, 31, 490; DOI: https://doi.org/10.1016/j.mencom.2021.07.017.

    Article  CAS  Google Scholar 

  4. K. S. Rodygin, V. V. Voronin, M. S. Ledovskaya, Russ. Chem. Bull., 2020, 69, 1401; DOI https://doi.org/10.1007/s11172-020-2915-3.

    Article  CAS  Google Scholar 

  5. J. P. Kamerling, G. Strecker, J.-P. Farriaux, L. Dorland, J. Haverkamp, J. F. G. Vliegenthart, Biochim. Biophys. Acta, Gen. Subj., 1979, 583, 403; DOI: https://doi.org/10.1016/0304-4165(79)90465-3.

    Article  CAS  Google Scholar 

  6. A. G. Santana, G. Vadlamani, B. L. Mark, S. G. Withers, Chem. Commun., 2016, 52, 7943; DOI: https://doi.org/10.1039/c6cc02520j.

    Article  CAS  Google Scholar 

  7. V. O. Kur’yanov, T. A. Chupakhina, O. V. Shishkin, S. V. Shishkina, V Ya. Chirva, Russ. J. Bioorg. Chem. (Engl. Transl.), 2008, 34, 730; DOI: https://doi.org/10.1134/S1068162008060137.

    Article  Google Scholar 

  8. A. Cardona, O. Boutureira, S. Castillón, Y. Díaz, M. I. Matheu, Green Chem., 2017, 19, 2687; DOI: https://doi.org/10.1039/c7gc00722a.

    Article  CAS  Google Scholar 

  9. I. V. Myachin, A. V. Orlova, L. O. Kononov, Russ. Chem. Bull., 2019, 68, 2126; DOI: https://doi.org/10.1007/s11172-019-2677-y.

    Article  CAS  Google Scholar 

  10. S. S. Pertel, S. A. Seryi, E. S. Kakayan, A. I. Zinin, L. O. Kononov, Carbohydr. Res., 2022, 520, 108633; DOI: https://doi.org/10.1016/j.carres.2022.108633.

    Article  CAS  Google Scholar 

  11. W. Priebe, G. Grynkiewicz, in Glycoscience: Chemistry and Chemical Biology, Eds B. O. Fraser-Reid, K. Tatsuta, J. Thiem, Springer Berlin Heidelberg, Berlin, Heidelberg, 2001, p. 748; DOI: https://doi.org/10.1007/978-3-642-56874-9_23.

  12. D. J. Chambers, G. R. Evans, A. J. Fairbanks, Tetrahedron, 2004, 60, 8411; DOI: https://doi.org/10.1016/j.tet.2004.07.005.

    Article  CAS  Google Scholar 

  13. N. Pravdic, I. Franjic-Mihalic, B. Danilov, Carbohydr. Res., 1975, 45, 302; DOI: https://doi.org/10.1016/S0008-6215(00)85889-9.

    Article  CAS  Google Scholar 

  14. W. Salo, H. G. Fletcher, J. Org. Chem., 1969, 34, 3189; DOI: https://doi.org/10.1021/JO01262A082.

    Article  CAS  Google Scholar 

  15. M. R. E. S. Aly, E. S. H. El Ashry, Adv. Carbohydr. Chem. Biochem., 2016, 73, 117; DOI: https://doi.org/10.1016/bs.accb.2016.08.001.

    Article  Google Scholar 

  16. S. S. Pertel, L. O. Kononov, A. I. Zinin, Va. Chirva, E. S. Kakayan, Carbohydr. Res., 2012, 356, 172; DOI: https://doi.org/10.1016/j.carres.2012.03.026.

    Article  CAS  Google Scholar 

  17. V. Fauré-Tromeur, S. Z. Zard, Tetrahedron Lett., 1999, 40, 1305; DOI: https://doi.org/10.1016/S00404039(98)02669-0.

    Article  Google Scholar 

  18. C. Mao, Z. Wang, Z. Wang, P. Ji, J.-P. Cheng, J. Am. Chem. Soc., 2016, 138, 5523; DOI: https://doi.org/10.1021/jacs.6b02607.

    Article  CAS  Google Scholar 

  19. R. U. Lemieux, H. Driguez, J. Am. Chem. Soc., 1975, 97, 4063; DOI: https://doi.org/10.1021/ja00847a033.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. S. Pertel.

Additional information

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2021–2023, September, 2022.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pertel, S.S., Kakayan, E.S., Seryi, S.A. et al. New method for the synthesis of 2-acylamino glycals. Russ Chem Bull 71, 2021–2023 (2022). https://doi.org/10.1007/s11172-022-3624-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-022-3624-x

Key words

Navigation