Skip to main content
SpringerLink
Log in

An Expedient Method for Kinetically Controlled Acetonide Formation from d-Fructose Induced by Ionic Liquid Catalyst Accompanied with SrCl2·6H2O

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The present work was undertaken to ascertain whether IL-metal salt catalyzed isopropylidenation of d-fructose yield desired acetonides. For the first time, an imidazole based ionic liquid compound accompanied with strontium chloride has been identified as a suitable dual catalyst system for the chemoselective O-isopropylidenation of d-fructose with acetone. In the present protocol, mainly the kinetically controlled less stable cyclic ketal 1,2;4,5-di-O-isopropylidene-β-d-fructopyranose is formed as an initial product with satisfactory yield and without isomerization to the thermodynamically more stable cyclic ketal 2,3;4,5-di-O-isopropylidene-β-d-fructopyranose. Therefore, this protocol is more advantageous compared to other mineral acid catalyzed protocols that require more sensitive reaction conditions.

Graphic Abstract

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Pétursson S (1997) J Chem Educ 74:1297–1303

    Article  Google Scholar 

  2. Kang J, Lim GJ, Yoon SK, Kim MY (1995) J Org Chem 60:564–577

    Article  CAS  Google Scholar 

  3. Tu Y, Frohn M, Wang ZX, Shi Y (2003) Org Synth 80:1

    Article  CAS  Google Scholar 

  4. Wang ZX, Tu Y, Frohn M, Zhang JR, Shi Y (1997) J Am Chem Soc 119:11224–11235

    Article  CAS  Google Scholar 

  5. Costa PRR, Ferreira VF, Alencar KG, Filho HCA, Ferreira CM, Pinheiro S (1996) J Carbohydr Chem 15:691–699

    Article  CAS  Google Scholar 

  6. Vanlaldinpuia K, Bora P, Bez G (2017) J Chem Sci 129:301–312

    Article  CAS  Google Scholar 

  7. Huang H, Liu X, Chen S, Chen H, Zheng Z (2004) Tetrahedron: Asymmetry 15:2011–2019

    Article  CAS  Google Scholar 

  8. Vennam RDK, Thatipamula RK, Haridasyam SB, Koppula SK (2018) Chem Heterocycl Comp 54:630–637

    Article  CAS  Google Scholar 

  9. Veleti SK, Lindenberger JJ, Thanna S, Ronning DR, Sucheck SJ (2014) J Org Chem 79:9444–9450

    Article  CAS  Google Scholar 

  10. Maryanoff BE, Nortey SO, Gardock JF, Shank RP, Dodgson SP (1987) J Med Chem 30:880–887

    Article  CAS  Google Scholar 

  11. Beksan E, Schieberle P, Robert F, Blank I, Fay LB, Cerny HS, Hofmann T (2003) J Agric Food Chem 51:5428–5436

    Article  CAS  Google Scholar 

  12. Dag A, Callari M, Lua H, Stenzel MH (2016) Polym Chem 7:1031–1036

    Article  CAS  Google Scholar 

  13. Zhao J, Babiuch K, Lu H, Dag A, Gottschaldt M, Stenzel MH (2014) Chem Commun 50:15928–15931

    Article  CAS  Google Scholar 

  14. Kiso M, Hasegawa A (1976) Carbohydr Res 52:95–101

    Article  CAS  Google Scholar 

  15. Singh PP, Gharia MM, Dasgupta F, Srivastava HC (1977) Tetrahedron Lett 18:439–440

    Article  Google Scholar 

  16. Kartha KPR (1986) Tetrahedron Lett 27:3415–3416

    Article  CAS  Google Scholar 

  17. Rauter AR, Ribeiro FR, Fernandes AC, Figueiredo JA (1995) Tetrahedron 51:6529–6540

    Article  CAS  Google Scholar 

  18. Asakura J, Matsubara Y, Yoshihara M (1996) J Carbohydr Chem 15:231–239

    Article  CAS  Google Scholar 

  19. Manzo E, Barone G, Parrilli M (2000) Synlett 2000:887–889

    Article  Google Scholar 

  20. Rajput VK, Mukhopadhyay B (2006) Tetrahedron Lett 47:5939–5941

    Article  CAS  Google Scholar 

  21. Lin CC, Jan MD, Weng SS, Lin CC, Chen CT (2006) Carbohydr Res 341:1948–1953

    Article  CAS  Google Scholar 

  22. Khan AT, Khan MM (2010) Carbohydr Res 345:154–159

    Article  CAS  Google Scholar 

  23. Khan AT, Khan MM, Adhikary A (2011) Carbohydr Res 346:673–677

    Article  CAS  Google Scholar 

  24. Mandal S, Verma PR, Mukhopadhyay B, Gupta P (2011) Carbohydr Res 346:2007–2010

    Article  CAS  Google Scholar 

  25. Vanlaldinpuia K, Bez G (2011) Tetrahedron Lett 52:3759–3764

    Article  CAS  Google Scholar 

  26. Rong YW, Zhang QH, Wang W, Li BL (2014) Bull Korean Chem Soc 35:2165–2168

    Article  CAS  Google Scholar 

  27. Rokade SM, Bhate PM (2017) J Carbohydr Chem 36:20–30

    Article  CAS  Google Scholar 

  28. Hough L, Richardson AC (1967) In: Coffey S (ed) Rodd’s Chemistry of Carbon Compounds, vol I-F. Elsevier, Amsterdam, p 356

    Google Scholar 

  29. Brady RF (1970) Carbohydr Res 15:35–40

    Article  CAS  Google Scholar 

  30. Banks MR, Cadogan JIG, Gosney I, Gould RO, Hodgson PKG, McDougall D (1998) Tetrahedron 54:9765–9784

    Article  CAS  Google Scholar 

  31. Meng XB, Li YF, Li Z (2007) J Carbohydr Res 342:1101–1104

    Article  CAS  Google Scholar 

  32. Ohle H (1924) Ber Dtsch Chem Ges 57:1566–1576

    Article  Google Scholar 

  33. Verhart CGJ, Caris BMG, Zwanenburg B, Chittenden GJF (1992) Recl Trav Chim Pays-Bas 111:348–352

    Article  CAS  Google Scholar 

  34. Pedatella S, Guaragna A, D’Alonzo D, De Nisco M, Palumbo G (2006) Synthesis 2005:305–308

    Google Scholar 

  35. Yıldırım A, Mudaber S, Öztürk S (2019) Eur J Lipid Sci Technol 121:1800303

    Google Scholar 

  36. Polchow K, Voss J (2005) Phosphorus Sulfur Silicon Relat Elem 180:1755–1768

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Bursa Uludağ University, Bursa, Turkey

    Ayhan Yıldırım

Authors
  1. Ayhan Yıldırım
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ayhan Yıldırım.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 1691 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yıldırım, A. An Expedient Method for Kinetically Controlled Acetonide Formation from d-Fructose Induced by Ionic Liquid Catalyst Accompanied with SrCl2·6H2O. Catal Lett 150, 2566–2571 (2020). https://doi.org/10.1007/s10562-020-03175-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-020-03175-2

Keywords

Search

Navigation