Skip to main content
SpringerLink
Log in

Orthoesters of sugars

Communication 11. Alkali-catalyzed cyclization of 1,2-allylorthoacetyl- and 1,2-allylorthobenzoyl-α-D-glucopyranose to trigyclic 1,2,4-orthoesters of α-D-glucopyranose and synthesis of 1,2,4-orthoacetyl-3,6-anhydro-α-D-glucopyranose

  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A new reaction of the orthoesters of sugars was discovered, namely the alkali-catalyzed cyclization of the allyl 1,2-orthoesters ofα-D-glucopyranose to the tricyclic 1,2,4-orthoesters of α-D-gluoopyranose.

  2. 2.

    1,2,4-Orthoacetyl-3,6-anhydro-α-D-glucopyranose, a tetracyclic member of skeletonheterocyclic systems, was synthesized.

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. A. F. Bochkov, V. I. Betaneli, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim.,1974, 1379.

  2. N. K. Kochetkov and A. F. Bochkov, Recent Developments in the Chemistry of Natural Carbon Compounds, Vol. 4, Akademia Kiado, Budapest (1971), p. 79.

    Google Scholar 

  3. V. V. Mezedvitskii, E. P. Olekhnovich, and G. N. Dorofeenko, Usp. Khim.,42, 896 (1973).

    Google Scholar 

  4. R. H. DeWolfe, Synthesis,3, 153 (1974).

    Google Scholar 

  5. B. Helferich and K. Weis, Chem. Ber.,89, 314 (1956).

    Google Scholar 

  6. N. K. Kochetkov, A. J. Khorlin, and A. F. Bochkov, Tetrahedron,23, 693 (1967).

    Google Scholar 

  7. A. F. Bochkov, V. I. Snyatkova, Ya. V. Voznyi, and N. K. Kochetkov, Zh. Obshch. Khim.,42, 2776 (1971).

    Google Scholar 

  8. A. F. Bochkov, I. V. Obruchnikov, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim.,1971, 1282.

  9. A. F. Bochkov, I. V. Obruchnikov, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim.,1971, 1291.

  10. J. Cunningham, R. Gigg, and C. D. Warren, Tetrahedron Lett.,1964, 1191.

  11. A. F. Bochkov, V. M. Dashunin, A. V. Kessenikh, V. A. Korenevskii, N. K. Kochetkov, A. D. Naumov, I. V. Obruchnikov, and E. P. Prokof'ev, Zh. Obshch. Khim.,41, 2770 (1971).

    Google Scholar 

  12. N. K. Kochetkov, A. Ya. Khorlin, A. F. Bochkov, and I. G. Yazlovetskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1966, 2030.

  13. A. F. Bochkov, I. V. Obruchnikov, and N. K. Kochetkov, Zh. Obshch. Khim.,42, 2776 (1972).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    A. F. Bochkov, Ya. V. Voznyi, V. M. Kalinevich, A. S. Shashkov & N. K. Kochetkov

Authors
  1. A. F. Bochkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ya. V. Voznyi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. M. Kalinevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. S. Shashkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. K. Kochetkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for Communication 10.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 415–420, February, 1975.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bochkov, A.F., Voznyi, Y.V., Kalinevich, V.M. et al. Orthoesters of sugars. Russ Chem Bull 24, 343–347 (1975). https://doi.org/10.1007/BF00925783

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00925783

Keywords

Search

Navigation