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Russian Journal of Organic Chemistry

, Volume 49, Issue 3, pp 366–373 | Cite as

Synthesis and asymmetric oxidation of thioglycosides derived from neomenthanethiol and α-d-galactose

  • S. V. PestovaEmail author
  • D. V. Sudarikov
  • S. A. Rubtsova
  • A. V. Kutchin
Article

Abstract

6-Deoxy-6-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexylsulfanyl]-1,2:3,4-di-O-isopropylidene-α-d-galactopyranose was synthesized in 94% yield from 1,2 : 3,4-di-O-isopropylidene-α-d-galactopyranose and neomenthanethiol, and its oxidation gave the corresponding diastereoisomeric sulfoxides in up to 84% yield and de values of up to 52%. The isopropylidene protective groups were removed from the sulfide and sulfoxides by treatment with trifluoroacetic acid in chloroform.

Keywords

Acac TBHP Sulfinyl Galactopyranose Cumyl Hydroperoxide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Herzallah, S. and Holley, R., LWT Food Sci. Technol., 2012, vol. 47, p. 293.CrossRefGoogle Scholar
  2. 2.
    Aversa, M.C., Barattucci, A., and Bonaccorsi, P., Tetrahedron, 2008, vol. 64, p. 7659.CrossRefGoogle Scholar
  3. 3.
    Aversa M.C., Barattucci, A., Bilardo, M.C., Bonaccorsi, P., Giannetto, P., Rollin, P., and Tatibouët, A., J. Org. Chem., 2005, vol. 70, p. 7389.CrossRefGoogle Scholar
  4. 4.
    Duclos, R.I., Jr., Lu, D., Guo, J., and Makriyannis, A., Tetrahedron Lett., 2008, vol. 49, p. 5587.CrossRefGoogle Scholar
  5. 5.
    Meyring, M., Mühlbacher, J., Messer, K., KastnerPustet, N., Bringmann, G., Mannschreck, A., and Blaschke, G., Anal. Chem., 2002, vol. 74, p. 3726.CrossRefGoogle Scholar
  6. 6.
    Fernández, I. and Khiar, N., Chem. Rev., 2003, vol. 103, p. 3651.CrossRefGoogle Scholar
  7. 7.
    Demakova, M.Ya., Sudarikov, D.V., Rubtsova, S.A., Slepukhin, P.A., and Kutchin, A.V., Russ. J. Org. Chem., 2012, vol. 48, p. 113.CrossRefGoogle Scholar
  8. 8.
    Izmest’ev, E.C., Sudarikov, D.V., Rubtsova, S.A., Slepukhin, P.A., and Kutchin, A.V., Russ. J. Org. Chem., 2012, vol. 48, p. 184.CrossRefGoogle Scholar
  9. 9.
    Garegg, P.J. and Samuelsson, B., J. Chem. Soc., Perkin Trans. 1, 1980, p. 2866.Google Scholar
  10. 10.
    Ohle, H. and Berend, G., Ber., 1925, vol. 58, p. 2585.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • S. V. Pestova
    • 1
    Email author
  • D. V. Sudarikov
    • 1
  • S. A. Rubtsova
    • 1
  • A. V. Kutchin
    • 1
  1. 1.Institute of Chemistry, Komi Research Center, Ural BranchRussian Academy of SciencesSyktyvkarRussia

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