Skip to main content

Ionic Liquids as Green Solvents for Glycosylation Reactions

  • Chapter
  • First Online:
Green Solvents II

Abstract

This chapter deals with how we took advantages of unique properties of ionic liquids in glycosylation reactions, such as their tunability, basicity of anion moieties, and nonvolatility. Thus, we developed environmentally benign O- and C-glycosylation methods using glycosyl phosphates, glycosyl fluorides, methyl glycosides, and 1-hydroxy sugars in several ionic liquids.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Jain N, Kumar A, Chauhan S, Chauhan SMS (2005) Chemical and biochemical transformations in ionic liquids. Tetrahedron 61:1015–1060

    Article  CAS  Google Scholar 

  2. Pârvulescu VI, Hardacre C (2007) Catalysis in ionic liquids. Chem Rev 107:2615–2665

    Article  Google Scholar 

  3. Plechkova NV, Seddon KR (2008) Applications of ionic liquids in the chemical industry. Chem Soc Rev 37:123–150

    Article  CAS  Google Scholar 

  4. Jiang T, Han B (2009) Ionic liquid catalytic systems and chemical reactions. Curr Org Chem 13:1278–1299

    Article  CAS  Google Scholar 

  5. Ni B, Headley AD (2010) Ionic-liquid-supported (ILS) catalysts for asymmetric organic synthesis. Chem-Eur J 16:4426–4436

    Article  CAS  Google Scholar 

  6. Lee SG (2006) Functionalized imidazolium salts for task-specific ionic liquids and their applications. Chem Commun 14(10):1049–1063

    Article  Google Scholar 

  7. Liu Y, Wang S-S, Liu W, Wan Q-X, Wu H-H, Gao G-H (2009) Transition-metal catalyzed carbon–carbon couplings mediated with functionalized ionic liquids, supported-ionic liquid phase, or ionic liquid media. Curr Org Chem 13:1322–1346

    Article  CAS  Google Scholar 

  8. Toshima K (2006) Novel glycosylation methods and their application to natural products synthesis. Carbohydr Res 341:1282–1297

    Article  CAS  Google Scholar 

  9. Yadav JS, Subba Reddy BV, Reddy JSS (2002) Dy(OTf)3-immobilized in ionic liquids: a novel and recyclable reaction media for the synthesis of 2,3-unsaturated glycopyranosides. J Chem Soc Perkin Trans 1:2390–2394

    Article  Google Scholar 

  10. Rencurosi A, Lay L, Russo G, Caneva E, Poletti L (2006) NMR evidence for the participation of triflated ionic liquids in glycosylation reaction mechanisms. Carbohydr Res 341:903–908

    Article  CAS  Google Scholar 

  11. Rencurosi A, Lay L, Russo G, Caneva E, Poletti L (2005) Glycosylation with trichloroacetimidates in ionic liquids: influence of the reaction medium on the stereochemical outcome. J Org Chem 70:7765–7768

    Article  CAS  Google Scholar 

  12. Poletti L, Rencurosi A, Lay L, Russo G (2003) Trichloroacetimidates as glycosyl donors in recyclable ionic liquids. Synlett 2003:2297–2300

    Article  Google Scholar 

  13. Pakulski Z (2003) Glycosylation in ionic liquids. Synthesis 13:2074–2078

    Article  Google Scholar 

  14. Sasaki K, Nagai H, Matsumura S, Toshima K (2003) A novel greener glycosidation using an acid-ionic liquid containing a protic acid. Tetrahedron Lett 44:5605–5608

    Article  CAS  Google Scholar 

  15. S-i H, Sano A, Sakamoto H, Nakajima M, Yanagiya Y, Ikegami S (1995) An attempt at the direct construction of 2-deoxy-β-glycosidic linkages capitalizing on 2-deoxyglycopyranosyl diethyl phosphites as glycosyl donors. Synlett 1995:1271–1273

    Article  Google Scholar 

  16. S-i H, Umeo K, Sano A, Watanabe N, Nakajima M, Ikegami S (1995) An extremely mild and stereocontrolled construction of 1,2-trans-β-glycosidic linkages capitalizing on benzyl-protected glycopyranosyl diethyl phosphites as glycosyl donors. Tetrahedron Lett 36:2251–2254

    Article  Google Scholar 

  17. Sakamoto H, Nakamura S, Tsuda T, Hashimoto S (2000) Chemoselective glycosidation strategy based on glycosyl donors and acceptors carrying phosphorus-containing leaving groups: a convergent synthesis of ganglioside GM3. Tetrahedron Lett 41:7691–7695

    Article  CAS  Google Scholar 

  18. Kondo H, Aoki S, Ichikawa Y, Halcomb RL, Ritzen H, Wong C-H (1994) Glycosyl phosphites as glycosylation reagents: scope and mechanism. J Org Chem 59:864–877

    Article  CAS  Google Scholar 

  19. Kondo H, Ichikawa Y, Wong CH (1992) β-Sialyl phosphite and phosphoramidite: synthesis and application to the chemoenzymatic synthesis of CMP-sialic acid and sialyl oligosaccharides. J Am Chem Soc 114:8748–8750

    Article  CAS  Google Scholar 

  20. Sim MM, Kondo H, Wong CH (1993) Synthesis of dibenzyl glycosyl phosphites using dibenzyl N, N-diethylphosphoramidite as phosphitylating reagent: an effective route to glycosyl phosphates, nucleotides, and glycosides. J Am Chem Soc 115:2260–2267

    Article  CAS  Google Scholar 

  21. Watanabe Y, Nakamoto C, Ozaki S (1993) Glycosidation based on phosphite chemistry. Synlett 115–116

    Google Scholar 

  22. Watanabe Y, Nakamoto C, Yamamoto T, Ozaki S (1994) Glycosylation using glycosyl phosphite as a glycosyl donor. Tetrahedron 50:6523–6536

    Article  CAS  Google Scholar 

  23. Tanaka H, Sakamoto H, Sano A, Nakamura S, Nakajima M, Hashimoto S (1999) An extremely mild and stereocontrolled construction of 1,2-cis-alpha-glycosidic linkages via benzyl-protected glycopyranosyl diethyl phosphites. Chem Commun 1259–1260

    Google Scholar 

  24. Mukaiyama T, Murai Y, Shoda S (1981) An efficient method for glucosylation of hydroxy compounds using glucopyranosyl fluoride. Chem Lett 10:431–432

    Article  Google Scholar 

  25. Sasaki K, Matsumura S, Toshima K (2004) A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity. Tetrahedron Lett 45:7043–7047

    Article  CAS  Google Scholar 

  26. Jona H, Mandai H, Chavasiri W, Takeuchi K, Mukaiyama T (2002) Protic acid catalyzed stereoselective glycosylation using glycosyl fluorides. Bull Chem Soc Jpn 75:291–309

    Article  CAS  Google Scholar 

  27. Avent AG, Chaloner PA, Day MP, Seddon KR, Welton T (1994) Evidence for hydrogen bonding in solutions of 1-ethyl-3-methylimidazolium halides, and its implications for room-temperature halogenoaluminate(III) ionic liquids. J Chem Soc Dalton Trans 3405–3413

    Google Scholar 

  28. Hashimoto S, Hayashi M, Noyori R (1984) Glycosylation using glucopyranosyl fluorides and silicon–based catalysts. Solvent dependency of the stereoselection. Tetrahedron Lett 25:1379–1382

    Article  CAS  Google Scholar 

  29. Yamada C, Sasaki K, Matsumura S, Toshima K (2007) Aryl C-glycosylation using an ionic liquid containing a protic acid. Tetrahedron Lett 48:4223–4227

    Article  CAS  Google Scholar 

  30. Sasaki K, Matsumura S, Toshima K (2006) An efficient glycosidation method using 2,3-unsaturated glycosyl donors. Tetrahedron Lett 47:9039–9043

    Article  CAS  Google Scholar 

  31. Sasaki K, Matsumura S, Toshima K (2007) Toward the total synthesis of vineomycin B2: application of an efficient glycosylation methodology using 2,3-unsaturated sugars. Tetrahedron Lett 48:6982–6986

    Article  CAS  Google Scholar 

  32. Yoshimura Y, Shimizu H, Hinou H, Nishimura S (2005) A novel glycosylation concept; microwave-assisted acetal-exchange type glycosylations from methyl glycosides as donors. Tetrahedron Lett 46:4701–4705

    Article  CAS  Google Scholar 

  33. Vidadala SR, Hotha S (2009) Methyl glycosides are identified as glycosyl donors for the synthesis of glycosides, disaccharides and oligosaccharides. Chem Commun 18:2505–2507

    Article  Google Scholar 

  34. Toshima K, Nagai H, Matsumura S (1999) Novel dehydrative glycosidations of 1-hydroxy sugars using a heteropoly acid. Synlett 9:1420–1422

    Article  Google Scholar 

  35. Jona H, Mandai H, Mukaiyama T (2001) A catalytic and stereoselective glycosylation with glucopyranosyl fluoride by using various protic acids. Chem Lett 5:426–427

    Article  Google Scholar 

  36. Gin D (2002) Dehydrative glycosylation with 1-hydroxy donors. J Carbohydr Chem 21:645–665, and references cited therein

    Article  CAS  Google Scholar 

  37. Suzuki T, Watanabe S, Yamada T, Hiroi K (2003) Dehydrative glycosylation of tri-O-benzylated 1-hydroxyribofuranose catalyzed by a copper(II) complex. Tetrahedron Lett 44:2561–2563

    Article  CAS  Google Scholar 

  38. Nishida Y, Shingu Y, Dohi H, Kobayashi K (2003) One-pot a-glycosylation method using appel agents in N, N-dimethylformamide. Org Lett 5:2377–2380

    Article  CAS  Google Scholar 

  39. Wagner B, Heneghan M, Schnabel G, Ernst B (2003) Catalytic glycosylation with rhodium(III)-triphos catalysis. Synlett 9:1303–1306

    Google Scholar 

  40. Kim KS, Fulse DB, Baek JY, Lee B-Y, Jeon HB (2008) Stereoselective direct glycosylation with anomeric hydroxy sugars by activation with phthalic anhydride and trifluoromethanesulfonic anhydride involving glycosyl phthalate intermediates. J Am Chem Soc 130:8537–8547

    Article  CAS  Google Scholar 

  41. Kuroiwa Y, Sekine M, Tomono S, Takahashi D, Toshima K (2010) A novel glycosylation of inactive glycosyl donors using an ionic liquid containing a protic acid under reduced pressure conditions. Tetrahedron Lett 51:6294–6297

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors want to thank all the coworkers who have worked on this project presented here, Dr. Hideyuki Nagai, Ms. Chigusa Yamada, Mr. Yoshitaka Kuroiwa, Mr. Satoshi Tomono, and Ms. Maiko Sekine in Keio University, Japan.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kazunobu Toshima .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Sasaki, K., Takahashi, D., Toshima, K. (2012). Ionic Liquids as Green Solvents for Glycosylation Reactions. In: Mohammad, A., Inamuddin, D. (eds) Green Solvents II. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-2891-2_3

Download citation

Publish with us

Policies and ethics