[R 4N] [AOT]: A surfactant ionic liquid as a mild glycosylation promoter

Journal of Carbohydrate Chemistry

Volumn 30, Issue 7-9, 2011, Pages 486-497

  Galan, M Carmen ^a   Tran, Anh Tuan ^a   Boisson, Julien ^a   Benito, David ^a   Butts, Craig ^a   Eastoe, Julian ^a   Brown, Paul ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Glycosylation; Ionic liquids; Oligosaccharides; Surfactant ionic liquids

Indexed keywords

EID: 84856349208     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328303.2011.609626     Document Type: Article

References (49)

1. Galan, M.C.; Benito-Alifonso, D.;Watt, G.M. Carbohydrates in drug discovery. Org. Biomol. Chem. 2011, 9(10), 3598-3610.
2. Smoot, J.T.; Demchenko, A.V. Oligosaccharide synthesis: from conventional methods to modern expeditious strategies. Adv. Carbohydr. Chem. Biochem. 2009, 62, 161-250.
3. Zhu, X.M.; Schmidt, R.R. New principles for glycoside-bond formation. Angew. Chem. Int. Ed. 2009, 48, 1900-1934.
4. Sheldon, R. Catalytic reactions in ionic liquids. Chem. Commun. 2001, 2399-2407. (Pubitemid 33124059)
5. Dominguez de Maria, P. 'Nonsolvent' applications of ionic liquids in biotransformations and organocatalysis. Angew. Chem. Int. Ed. 2008, 47, 6960-6968.
6. El Seoud, O.A.; Koschella, A.; Fidale, L.C.; Dorn, S.; Heinze, T. Applications of ionic liquids in carbohydrate chemistry: A window of opportunities. Biomacromolecules 2007, 8, 2629-2647. (Pubitemid 47516909)
7. Hallett, J.P.;Welton, T. Room-temperature ionic liquids: Solvents for synthesis and catalysis. 2, Chem. Rev. 2011, 111, 3508-3576.
8. Murugesan, S.; Linhardt, R.J. Ionic liquids in carbohydrate chemistry - current trends and future directions. Curr. Org. Synth. 2005, 2, 437-451.
9. Forsyth, S.A.; MacFarlane, D.R.; Thomson, R.J.; von Itzstein, M. Rapid, clean, and mild O-acetylation of alcohols and carbohydrates in an ionic liquid. Chem. Commun. 2002, 714-715. (Pubitemid 34309809)
10. Rencurosi, A.; Lay, L.; Russo, G.; Caneva, E.; Poletti, L. Glycosylation with trichloroacetimidates in ionic liquids: Influence of the reaction medium on the stereochemical outcome. J. Org. Chem. 2005, 70, 7765-7768. (Pubitemid 41318541)
11. Sasaki, K.; Nagai, H.; Matsumura, S.; Toshima, K. A novel greener glycosidation using an acid-ionic liquid containing a protic acid. Tetrahedron Lett. 2003, 44, 5605-5608. (Pubitemid 36782589)
12. Galan, M.C.; Brunet, C.; Fuensanta, M. [bmim][OTf]: A versatile room temperature glycosylation promoter. Tetrahedron Lett. 2009, 50, 442-445.
13. Galan, M.C.; Jouvin, K.; Alvarez-Dorta, D. Scope and limitations of imidazoliumbased ionic liquids as room temperature glycosylation promoters. Carbohydr. Res. 2010, 345, 45-49.
14. Galan, M.C.; Tran, A.T.; Bernard, C. Ionic-liquid-based catch and release mass spectroscopy tags for enzyme monitoring. Chem. Commun. 2010, 46, 8968-8970.
15. Galan, M.C.; Tran, A.T.; Whitaker, S. [bmim][OTf] as co-solvent/promoter in room temperature reactivity-based one-pot glycosylation reactions. Chem. Commun. 2010, 46, 2106-2108.
16. Tran, A.T.; Burden, R.A.; Racys, D.; Galan, M.C. Ionic catch and release oligosaccharide synthesis. Chem. Commun. 2011, 47, 4526-4528.
17. Aggarwal, V.K.; Emme, I.; Mereu, A. Unexpected side reactions of imidazoliumbased ionic liquids in the base-catalysed Baylis-Hillman reaction. Chem. Commun. 2002, 1612-1613. (Pubitemid 34775505)
18. Gorodetsky, B.; Ramnial, T.; Branda, N.R.; Clyburne, J.A.C. Electrochemical reduction of an imidazolium cation: A convenient preparation of imidazol-2-ylidenes and their observation in an ionic liquid. Chem. Commun. 2004, 1972-1973. (Pubitemid 39336027)
19. Chakraborty, A.; Saha, S.; Chakraborty, S. Effect of size of tetraalkylammonium counterions on the temperature dependent micellization of AOT in aqueous medium. Colloid Polym. Sci. 2008, 286, 927-934.
20. Brown, P.; Butts, C.; Dyer, R.; Eastoe, J.; Grillo, I.; Guittard, F.D.R.; Rogers, S.; Heenan, R. Anionic surfactants and surfactant ionic liquids with quaternary ammonium counterions. Langmuir. 2011, 27, 4563-4571.
21. Oscarson, S. Carbohydr. Chem. Biol. Carbohydrates in Chemistry and Biology, Series Ed. Ernst, B., Hart, G.W., Sinay, P. Wiley-VCH, Weinheim. 2000, 1, 93-116.
22. Ye, X.-S.; Sun, F.; Liu, M.; Li, Q.; Wang, Y.; Zhang, G.; Zhang, L.-H.; Zhang, X.-L. Synthetic iminosugar derivatives as new potential immunosuppressive agents. J. Med. Chem., 2005, 48, 3688-3691. (Pubitemid 40776842)
23. Rencurosi, A.; Lay, L.; Russo, G.; Caneva, E.; Poletti, L. NMR evidence for the participation of triflated ionic liquids in glycosylation reaction mechanisms. Carbohydr. Res. 2006, 341, 903-908.
24. Pougny, J.R.; Sinay, P. Reaction of glucopyranosyl with acetonitrile - applications to synthesis. Tetrahedron Lett. 1976, 4073-4076.
25. Lemieux, R.U.; Ratcliffe, R.M. Azidonitration of tri-O-acetyl-D-galactal. Can. J. Chem. Rev. Can. Chim. 1979, 57, 1244-1251.
26. Demchenko, A., Stauch, T.; Boons, G.J. Solvent and other effects on the stereoselectivity of thioglycoside glycosidations. Synlett 1997, 818.
27. Schmidt, R.R.; Behrendt, M.; Toepfer, A. Glycosyl imidates. 48. Nitriles as solvents in glycosylation reactions: Highly selective β-glycoside synthesis. Synlett 1990, 11, 694-696
28. Crich, D.; Patel, M. On the nitrile effect in L-rhamnopyranosylation. Carbohydr. Res. 2006, 341, 1467-1475. (Pubitemid 43795397)
29. Boltje, T.J.; Buskas, T.; Boons, G.-J. Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research. Nat. Chem. 2009, 1, 611-622.
30. Grayson, E.J.; Ward, S.J.; Hall, A.L.; Rendle, P.M.; Gamblin, D.P.; Batsanov, A.S.; Davis, B.G. Glycosyl disulfides: novel glycosylating reagents with flexible aglycon alteration. J. Org. Chem. 2005, 70, 9740-9754. (Pubitemid 41689135)
31. Chery, F.; Cassel, S.; Wessel, H.P.; Rollin, P. Synthesis of anomeric sulfimides and their use as a new family of glycosyl donors. Eur. J. Org. Chem. 2002, 171-180.
32. Ferrier, R.J.; Furneaux, R.H. Synthesis of 1,2-trans-related 1-thioglycoside esters. Carbohydr. Res. 1976, 52, 63-68.
33. Kov́ ac, P.; Lerner, L. Systematic chemical synthesis and N.M.R. spectra of methyl [alpha]-glycosides of isomalto-oligosaccharides and related compounds. Carbohydr. Res. 1988, 184, 87-112.
34. Zhang, Y.-M.; Mallet, J.-M.; Sinä y, P. Glycosylation using a one-electron-transfer, homogeneous reagent. Application to an efficient synthesis of the trimannosyl core of N-glycosylproteins. Carbohydr. Res. 1992, 236, 73-88. (Pubitemid 23013598)
35. Zissis, E.; Clingman, A.L.; Richtmyer, N.K. Glucose diphenyl dithioacetal, phenyl 1-thio-[alpha]-glucopyranoside, phenyl 1-thio-[alpha]- glucofuranoside, and some related compounds. Carbohydr. Res. 1966, 2, 461-469.
36. Benakli, K.; Zha, C.X.; Kerns, R.J. Oxazolidinone protected 2-amino-2-deoxy-Dglucose derivatives as versatile intermediates in stereoselective oligosaccharide synthesis and the formation of alpha-linked glycosides. J. Am. Chem. Soc. 2001, 123, 9461-9462. (Pubitemid 32900324)
37. Mootoo, D.R.; Konradsson, P.; Udodong, U.; Fraserreid, B. Armed and disarmed Npentenyl glycosides in saccharide couplings leading to oligosaccharides. J. Am. Chem. Soc. 1988, 110, 5583-5584.
38. Zhang, Z.Y.; Ollmann, I.R.; Ye, X.S.; Wischnat, R.; Baasov, T.; Wong, C.H. Programmable one-pot oligosaccharide synthesis. J. Am. Chem. Soc. 1999, 121, 734-753.
39. Friesen, R.W.; Danishefsky, S.J. On the controlled oxidative coupling of glycals - a new strategy for the rapid assembly of oligosaccharides. J. Am. Chem. Soc. 1989, 111, 6656-6660.
40. Kamat, M.N.; Demchenko, A.V. Revisiting the armed-disarmed concept rationale: S-benzoxazolyl glycosides in chemoselective oligosaccharide synthesis. Org. Lett. 2005, 7, 3215-3218. (Pubitemid 41059109)
41. Schmidt, T.H.; Madsen, R. Glycosylations directed by the armed-disarmed effect with acceptors containing a single ester group. Eur. J. Org. Chem. 2007, 3935-3941.
42. Douglas, N.L.; Ley, S.V.; Lucking, U.; Warriner, S.L. Tuning glycoside reactivity: new tool for efficient oligosaccharide synthesis. J. Chem. Soc. Perkin Trans. 1 1998, 51-65. (Pubitemid 128757882)
43. Mong, T.K.K.; Lee, H.K.; Duron, S.G.; Wong, C.H. Reactivity-based one-pot total synthesis of fucose GM(1) oligosaccharide: A sialylated antigenic epitope of small-cell lung cancer. Proc. Nat. Acad. Sci. U S A 2003, 100, 797-802. (Pubitemid 36183910)
44. Huang, L.J.; Wang, Z.; Huang, X.F. One-pot oligosaccharide synthesis: reactivity tuning by post-synthetic modification of aglycon. Chem. Commun. 2004, 1960-1961. (Pubitemid 39336021)
45. Kreuzer, M.; Thiem, J. The composition of oligosaccharides with glycosylfluorides during Lewis acid catalysis. Carbohydr. Res. 1986, 149, 347-361.
46. Valerio, S.; Iadonisi, A.; Adinolfi, M.; Ravida, A. Novel approaches for the synthesis and activation of thio- and selenoglycoside donors. J. Org. Chem. 2007, 72, 6097-6106. (Pubitemid 47205982)
47. Premathilake, H.D.; Mydock, L.K.; Demchenko, A.V. Superarming common glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection. J. Org. Chem. 2010, 75, 1095-1100.
48. Halcomb, R.L.; Danishefsky, S.J. On the direct epoxidation of glycals: Application of a reiterative strategy for the synthesis of beta-linked oligosaccharides. J. Am. Chem. Soc. 2002, 111, 6661-6666.
49. Andrews, C.W.; Rodebaugh, R.; FraserReid, B. A solvation-assisted model for estimating anomeric reactivity. Predicted versus observed trends in hydrolysis of Npentenyl glycosides. J. Org. Chem. 1996, 61, 5280-5289. (Pubitemid 126532237)