Reaction kinetics and mechanism of sulfuric acid-catalyzed acetolysis of acylated methyl l-ribofuranosides

European Journal of Organic Chemistry

Volumn , Issue 32, 2009, Pages 5666-5676

  Forsman, Jonas J ^a   Wärnå, Johan ^b   Murzin, Dmitry Yu ^b   Leino, Reko ^a  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

^b LABORATORY OF INDUSTRIAL CHEMISTRY AND REACTION ENGINEERING   (Finland)

Author keywords

Acetolysis; Carbohydrates; Kinetics; Nmr spectroscopy; Reaction mechanisms

Indexed keywords

EID: 70549108002     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900889     Document Type: Article

References (46)

1. R. U. Lemieux, W. P. Shyluk, G. Huber, Can. J Chem. 1954, 33, 148-162.
2. B. Capon, Chem. Rev. 1969, 69, 407-498.
3. B. Lindberg, Acta Chem. Scand. 1949, 3, 1153-1169.
4. E. P. Painter, J. Am. Chem. Soc. 1953, 75, 1137-1146.
5. a) M. Miljkovió, M. Marino-Habash, J Org. Chem. 1983, 48, 855-860;
6. b) M. Miljkovió, D. Yeagley, R Deslongchamps, Y. L. Dory, J Org. Chem. 1997, 62, 7597-7604.
7. a) J. Kaczmarek, M. Preyss, H. Lönnberg, J Szafranek, Carbohydr. Res. 1995, 279, 107-116;
8. b) J. Kaczmarek, Z. Kaczynski, Z. Trumpakaj, J Szafranek, M. Bogalecka, H. Lönnberg, Carbohydr. Res. 2000, 325, 16-29.
9. a) L. A. Agrofoglio, Curr. Org. Chem. 2006, 10, 333-362;
10. b) G. Gumina, Y. Chong, G.-Y. Song, C. K. Chu, Curr. Top. Med. Chem. 2002, 2, 1065-1086;
11. c) E. De Clercq, Mini-Rev. Med. Chem. 2002, 2, 163-175;
12. d) G. Gumina, Y. Chong, G.-Y. Song, C. K. Chu, FEMS Microbiol. Lett. 2001, 202, 9-15.
13. a) U. Niedballa, H. Vorbrüggen, Angew. Chem. Int. Ed. Engl. 1970, 9, 461-462;
14. b) U. Niedballa, H. Vorbrüggen, J. Org. Chem. 1974, 39, 3654-3660;
15. c) U. Niedballa, H. Vorbrüggen, J. Org. Chem. 1974, 39, 3660-3663;
16. d) U. Niedballa, H. Vorbrüggen, J. Org. Chem. 1974, 39, 3664-3667;
17. e) U. Niedballa, H. Vorbrüggen, J. Org. Chem. 1974, 39, 3668-3671;
18. f) U. Niedballa, H. Vorbrüggen, J. Org. Chem. 1974, 39, 3672-3674.
19. a) J. Kaczmarek, J. Szafranek, K. C. B. Wilkie, H. Lönnberg, Finn. Chem. Lett. 1987, 14, 171-177;
20. b) A. J. Bennet, M. L. Sinnot, W. S. S. Wijesundera, J. Chem. Soc. Perkin Trans. 2 1985, 1233-1236;
21. c) H. Lönnberg, A. Kankaanperä, K. Haapakka, Carbohydr. Res. 1977, 56, 277-287;
22. d) H. Lönnberg, A. Kulonpää, Acta Chem. Scand. A 1977, 31, 306-312.
23. V. Ferneres, M. Gelin, R. Boulch, L. Toupet, D. Plusquellec, Carbohydr. Res. 1998, 314, 79-83.
24. P. Zhang, Z. E. Dong, T. P. Cleary, Org. Process Res. Dev. 2005, 9, 583-592.
25. P. C. Kline, A. S. Serianni, J. Am. Chem. Soc. 1990, 112, 7373-7381.
26. K. P. R. Kartha, R. A. Field, Tetrahedron 1997, 53, 11753-11766.
27. H. G. Fletcher Jr., The Anomeric Tri-O-benzoyl- D-arabinofuranosyl Bromides. In Methods in Carbohydrate Chemistry (Eds.: R. L. Whistler, M. L. Wolfrom, J. N. BeMiller); Academic Press, New York, 1963, vol.2, p. 228.
28. H. Zinner, Chem. Ber. 1953, 86, 817-824.
29. E. D. Montgomery, R. M. Hann, C. S. Hudson, J. Am. Chem. Soc 1937, 59, 1124-1129.
30. J. J. Forsman, J. Warna, D. Yu. Murzin, R. Leino, Carbohydr. Res. 2009, 344, 1102-1109.
31. J. Janson, B. Lindberg, Acta Chem. Scand. 1960, 14, 877-881.
32. E. P. Painter, Chem. Ind. (London) 1965, 1380-1381.
33. L. Rosenfeld, C. E. Bailou, Carbohydr. Res. 1974, 32, 287-298.
34. a) C. Malm, L. Tanghe, Ind. Eng. Chem. Anal. Ed. 1942, 14, 940-942;
35. b) C. Malm, L. Tanghe, B. C. Laird, Ind. Eng. Chem. 1946, 38, 77-82;
36. c) C. Malm, L. Tanghe, Ind. Eng. Chem. 1955, 47, 995-999.
37. J. A. Hyatt, G. W. Tindall, Heterocycles 1993, 35, 227-234.
38. A. Štimac, J Kobe, Carbohydr. Res. 2000, 324, 149-160.
39. D. R. McPhail, J. R. Lee, B. Fraser-Reid, J. Am. Chem. Soc. 1992, 114, 1905-1906.
40. H. Haario, Modest 6.0 - A User's Guide, Prof Math, Helsinki, 2001.
41. H. Haario, E. Saksman, J Tamminen, Bernoulli 2001, 7, 223-242.
42. T. E. Walker, H. P. C. Hogenkamp, T. E. Needham, N. A. Matwiyoff, Biochemistry 1974, 13, 2650-2655.
43. R. Barker, H. G. Fletcher Jr., J Org. Chem. 1961, 26, 4605-4609.
44. T. Sato, T. Simadate, Y. Isido, Nippon Kagaku Zasshi 1960, 81, 1442-1444.
45. R. D. Guthrie, S. C. Smith, Chem. Ind. (London) 1968, 547-548.
46. K. S. Ramasamy, R. C. Tarn, J. Bard, D. R. Averett, J Med. Chem. 2000, 43, 1019-1028.