Skip to main content
SpringerLink
Log in

Application of oxone immobilized on montmorillonite for an efficient oxidation of mannose thioglycoside

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A new solid system based on montmorillonite supported oxone has been developed and used for the oxidation of thiomannoside. The oxidation properties of oxone immobilized on montmorillonite were affected by polarity of the solvent, resulting in the different sulfoxide to sulfone ratios as the products. Toluene was the only solvent favouring sulfone formation over sulfoxide. X-ray crystal structures of the starting compound as well as the corresponding sulfoxide (major epimer Rs) and sulfone are also reported.

Graphical Abstract

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

Fig. 1

Similar content being viewed by others

References

  1. Taylor JG, Li X, Oberthuer M, Zhu W, Kahne DE (2006) J Am Chem Soc 128:15084

    Article  CAS  Google Scholar 

  2. Mochizuki T, Kondo Y, Abe H, Taylor CW, Potter BVL, Matsuda A, Shuto S (2006) Org Lett 8:1455

    Article  CAS  Google Scholar 

  3. Martin-Lomas M, Khiar N, Garcia S, Koessler J-L, Nieto PM, Rademacher TW (2000) Chem Eur J 6:3608

    Article  CAS  Google Scholar 

  4. Lichtenthaler FW, Oberthuer M, Peters S (2001) Eur J Org Chem 20:3849

    Article  Google Scholar 

  5. Crich D, Vinod AU (2003) Org Lett 5:1297

    Article  CAS  Google Scholar 

  6. Mannerstedt K, Ekelöf K, Oscarson S (2007) Carbohydr Res 342:631

    Article  CAS  Google Scholar 

  7. Kaethip S, Demchenko AV (2011) J Org Chem 76:7388

    Article  Google Scholar 

  8. Moumé-Pymbock M, Crich DJ (2011) Org Chem 77:8905

    Article  Google Scholar 

  9. De Jong A-R, Hagen B, van der Ark V, Overkleeft HS, Codée JDC, van der Marel GA (2011) J Org Chem 77:108

    Article  Google Scholar 

  10. Poláková M, Šesták S, Lattová E, Petruš L, Mucha J, Tvaroška I, Kóňa J (2011) Eur J Med Chem 46:944

    Article  Google Scholar 

  11. Ayers B, Long B, Sim E, Smellie IA, Wilkinson BL, Fairbanks AJ (2009) Carbohydr Res 344:739

    Article  CAS  Google Scholar 

  12. Taylor RJK, McAllister GD, Franck RW (2006) Carbohydr Res 341:1298

    Article  CAS  Google Scholar 

  13. Leon EI, Martin A, Perez-Martin I, Quintanal LM, Suarez E (2010) Eur J Org Chem 27:5248

    Article  Google Scholar 

  14. Poláková M, Beláňová M, Petruš L, Mikušová K (2010) Carbohydr Res 345:1339

    Article  Google Scholar 

  15. Griffin FK, Paterson DE, Murphy PV, Taylor RJK (2002) Eur J Org Chem 7:1305

    Article  Google Scholar 

  16. Singer M, Lopez M, Bornaghi LF, Innocenti A, Vullo D, Supuran CT, Poulsen S-A (2009) Biorg Med Chem Lett 19:2273

    Article  CAS  Google Scholar 

  17. Chen M-Y, Patkar LN, Lin C-C (2004) J Org Chem 69:2884

    Article  CAS  Google Scholar 

  18. Chen M-Y, Patkar LN, Chen H-T, Lin C-C (2003) Carbohydr Res 338:1327

    Article  CAS  Google Scholar 

  19. Crich D, Cai W, Dai Z (2000) J Org Chem 65:1291

    Article  CAS  Google Scholar 

  20. Kakarla R, Dulina RG, Hatzenbuhler NT, Hiu YW, Sofia MJ (1996) J Org Chem 61:8347

    Article  CAS  Google Scholar 

  21. Fernandez-Mayoralas A, Marra A, Trumtel M, Veyrieres A, Sinay P (1989) Carbohydr Res 188:81

    Article  CAS  Google Scholar 

  22. Gervay J, Flaherty TM, Holmes D (1997) Tetrahedron 53:16355

    Article  CAS  Google Scholar 

  23. Belica PS, Franck RW (1998) Tetrahedron Lett 39:8225

    Article  CAS  Google Scholar 

  24. Priebe W, Grynkiewicz G (1991) Tetrahedron Lett 32:7353

    Article  CAS  Google Scholar 

  25. Agnihotri G, Misra AK (2006) Carbohydr Res 341:275

    Article  CAS  Google Scholar 

  26. Morais GR, Humphrey AJ, Falconer RA (2008) Tetrahedron 64:7426

    Article  CAS  Google Scholar 

  27. Kropp PJ, Breton GW, Fields JD, Tung JC, Loomis BR (2000) J Am Chem Soc 122:4280

    Article  CAS  Google Scholar 

  28. Hirano M, Ueno Y, Morimoto T (1995) Synth Commun 25:3125

    Article  CAS  Google Scholar 

  29. Hirano M, Tomaru J, Morimoto T (1991) Bull Chem Soc Jpn 64:3752

    Article  CAS  Google Scholar 

  30. Poláková M, unpublished results

  31. Aversa MC, Barattucci A, Bilardo MC, Bonaccorsi P, Giannetto P, Rollin P, Tatiboët A (2005) J Org Chem 70:7389

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the APVV-51-046505, APVV-0202/10, VEGA-2/0159/12, VEGA 1/0679/11 and VEGA-1/0962/12 grants and the Slovak State Program Project No. 2003SP200280203. Dr. Vladimír Puchart is appreciated for helpful discussion.

Author information

Authors and Affiliations

  1. Institute of Chemistry, Center for Glycomics, Slovak Academy of Sciences, Dúbravská cesta 9, 845 38, Bratislava, Slovakia

    Monika Poláková

  2. Institute of Inorganic Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 845 36, Bratislava, Slovakia

    Ľuboš Jankovič

  3. Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    Lenka Kucková & Jozef Kožíšek

Authors
  1. Monika Poláková
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ľuboš Jankovič
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lenka Kucková
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jozef Kožíšek
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Monika Poláková.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 2174 kb)

Supplementary data Characterization of the reaction mixture and Figure S1: representative 1H NMR spectrum; X-ray data and Figures S2,S3.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Poláková, M., Jankovič, Ľ., Kucková, L. et al. Application of oxone immobilized on montmorillonite for an efficient oxidation of mannose thioglycoside. Monatsh Chem 144, 969–973 (2013). https://doi.org/10.1007/s00706-013-0964-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-013-0964-0

Keywords

Search

Navigation