Skip to main content
SpringerLink
Log in

Conversion of ascorbigen and its derivatives to substituted 1-deoxy-1-(indolyl-3)-α-L-sorbopyranose

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A new reaction involving L-ascorbic acid have been found. Under the action of alkali, ascorbigen and its N-alkyl derivatives undergo cleavage of the lactone ring, decarboxylation, and rearrangement to give 1-deoxy-1-(inolyl-3)-α-L-sorbopyranose and its N-alkyl derivatives. The structures of the compounds obtained were confirmed by mass-spectroscopy and PMR spectroscopy.

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. V. I. Mukhanov, I. V. Yatseva, B. S. Kikot', Yu. Yu. Volodin, I. L. Kustova, N. A. Lesnaya, Z. P. Sof'ina, N. P. Ermakova, and M. N. Preobrazhenskaya, Bioorg. Khim., No. 4, 544 (1984).

    Google Scholar 

  2. K. G. A. Jackson and J. K. N. Jones, Can. J. Chem., 43, 450 (1965).

    Google Scholar 

  3. M. Barber, R. S. Bordoli, R. D. Sedgwick, and A. N. Tyler, Org. Mass Spectrom., 16, 256 (1981).

    Google Scholar 

  4. R. A. Khmel'nitskii, Khim. Geterotsikl. Soedin., No. 3, 291, (1974).

    Google Scholar 

  5. T. Radford and D. C. Dejong, Biochemical Applications of Mass Spectrometry, Ed. G. R. Waller and O. C. Dermer, N. Y.: Wiley Intersci., (1980) p. 256.

    Google Scholar 

  6. B. Schneider, F. W. Lichtenthaler, G. Steinle, and H. Schiweck, Ann. (1985) p. 2443.

Download references

Author information

Authors and Affiliations

  1. All-Union Oncologic Research Center, Academy of Medical Sciences of the USSR, 115478, Moscow

    I. L. Plikhtyak, I. V. Yartseva, N. A. Klyuev & M. N. Preobrazhenskaya

  2. A. N. Severtsova Institute of Evolutionary Morphology and Ecology of Animals, Academy of Sciences of the USSR, 117071, Moscow

    I. L. Plikhtyak, I. V. Yartseva, N. A. Klyuev & M. N. Preobrazhenskaya

Authors
  1. I. L. Plikhtyak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Yartseva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. A. Klyuev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. N. Preobrazhenskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiko Geterotsiklicheskikh Soedinenii, No. 5, pp. 607–610, May, 1989.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Plikhtyak, I.L., Yartseva, I.V., Klyuev, N.A. et al. Conversion of ascorbigen and its derivatives to substituted 1-deoxy-1-(indolyl-3)-α-L-sorbopyranose. Chem Heterocycl Compd 25, 504–507 (1989). https://doi.org/10.1007/BF00482493

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00482493

Keywords

Search

Navigation