Dialkyl imidazolium benzoates - Room temperature ionic liquids useful in the peracetylation and perbenzoylation of simple and sulfated saccharides

Synlett

Volumn , Issue 9 SPEC. ISS., 2003, Pages 1283-1286

  Murugesan, Saravanababu ^a   Karst, Nathalie ^b   Islam, Tasneem ^b   Wiencek, John M ^a   Linhardt, Robert J ^a,b  

^a UNIVERSITY OF IOWA   (United States)

^b E11 SSH   (United States)

Author keywords

Acylation; Carbohydrates; Ionic liquids; Microwave; Sulfated sugars

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM BENZOATE; 1 ETHYL 3 METHYLIMIDAZOLIUM BENZOATE; 1 HEXYL 3 METHYLIMIDAZOLIUM BENZOATE; ALKYL GROUP; BENZOIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; IMIDAZOLE DERIVATIVE; ION; ORGANIC SOLVENT; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; GEL CHROMATOGRAPHY; LIQUID; MOLECULAR STABILITY; PERACETYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STOICHIOMETRY; SULFATION; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 0037765623     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40336     Document Type: Article

References (17)

1. Capila, I.; Linhardt, R. J. Angew. Chem. Int. Ed. 2002, 41, 390.
2. Kerns, R. J.; Vlahov, I. R.; Linhardt, R. J. Carbohydr. Res. 1995, 267, 143.
3. Vogel, A. I. Vogel's textbook of practical organic chemistry, 5th ed.; Wiley: New York, 1984, 644.
4. Horton, W. J.; Stout, M. G. J. Org. Chem. 1962, 27, 830.
5. Chandrasekhar, S.; Ramachander, T.; Takhi, M. Tetrahedron Lett. 1998, 39, 3263.
6. Dupont, J.; Consorti, C. S.; Spencer, J. J. Braz. Chem. Soc. 2000, 11, 337.
7. Seddon, K. R. J. Chem. Tech. Biotechnol. 1997, 68, 351.
8. Sheldon, R. Chem. Commun. 2001, 2399.
9. Forsyth, A. S.; MacFarlane, D. R.; Thomson, R. J.; Itzstein, M. V. Chem Commun. 2002, 714.
10. Carlin, R. T.; De Long, H. C.; Fuller, J.; Trulove, P. C. J. Electrochem. Soc. 1994, 141, L73.
11. Holbrey, J. D.; Seddon, K. R. J. Chem. Soc., Dalton Trans. 1999, 2133.
12. Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 5381.
13. 2), 7.16 (1 H, t, J = 1.7 Hz, Im), 7.47 (2 H, m, Ph), 7.59 (1 H, m, Ph), 7.87 (1H, t, J = 1.8 Hz, Im), 7.93 (2 H, m, Ph), 9.24 (1 H, s, Im).
14. Foley, K. M.; Griffin, C. C.; Amaya, E. US. Pat. App, 898124, 1990.
15. Petitou, M.; Coudert, C.; Level, N.; Lormeau, J.-C.; Zuber, M.; Simenel, C.; Fournier, J.-P.; Choay, J. Carbohydr. Res. 1992, 236, 107.
16. 2O, 400 MHz) δ 4.39-4.69 (5.25 H, m, H-5α,β, H-6aα,β, H-6bα,β), 5.69 (1 H, dd, J = 3.7 Hz, 10.3 Hz, H-2α, 5.80-5.90 (2.5 H, m, H-4α, H-2β, H-4β), 6.05 (0.75 H, t, J = 9.4 Hz, H-3β), 6.30 (0.75 H, d, J = 7.9 Hz, H- 1β), 6.33 (1 H, t, d = 10.0 Hz, H-3α), 6.85 (1 H, d, d = 3.7 Hz, H-1α), 8.18-7.27 (25 H, m, Ar).
17. +].