Synthesis of homochiral 2-C-trifluoromethyl D- and L-ribose via trifluoromethylation of pentopyranosid-2-uloses

Journal of Heterocyclic Chemistry

Volumn 40, Issue 2, 2003, Pages 329-335

  Eilitz, Uwe ^a   Böttcher, Christoph ^a   Hennig, Lothar ^a   Burger, Klaus ^a   Haas, Alois ^b,c   Gockel, Simone ^b   Sieler, Joachim ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b RUHR UNIVERSITY BOCHUM   (Germany)

^c NONE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 C TRIFLUOROMETHYL DEXTRO RIBOSE; 2 C TRIFLUOROMETHYL LEVO RIBOSE; ALKENE DERIVATIVE; DEXTRO 3,4 O ISOPROPYLIDENE BETA ERYTHRO PENTOPYRANOSID 2 ULOSE; GLYCOSIDE; REAGENT; RIBOSE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; INFRARED SPECTROSCOPY; METHODOLOGY; METHYLATION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038710891     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570400221     Document Type: Article

References (45)

1. C. B. Reese and C. N. V. S. Varaprasad, J. Chem. Soc. Perkin Trans. I, 189 (1994).
2. [a] Y. Murai, H. Shiroto, T. Ishizaki, T. Iimori, Y. Kodama, Y. Ohtzuka and T. Oishi, Heterocycles, 33, 391 (1992);
3. [b] T. Iimori, Y. Murai, S. Ohuchi, Y. Kodama, Y. Ohtsuka and T. Oishi, Tetrahedron Lett., 32, 7273 (1991).
4. R. D. Chambers, Fluorine in Organic Chemistry, New York, Wiley & Sons 1973;
5. [b] J.T. Welch, Tetrahedron, 43, 3123 (1987);
6. [c] C. Schmidt, Synlett, 241 and 238 (1994).
7. N. F. Taylor, Fluorinated Carbohydrates, Chemical and Biological Aspects, ACS Symposium Series 374 (1988).
8. [a] N. Muller, J. Pharm. Sci., 75, 987 (1986);
9. [b] J. T. Welch, in: Selective Fluorination in Organic and Bioorganic Chemistry, J. T. Welch (ed), ACS Symposium Series, No 456, ACS Washington DC, (1991), and literature cited therein.
10. For a review see: R. Plantier-Royon and C. Portella, Carbohydrate Res., 327, 119 (2000).
11. For a review see: J. G. Riess and J. Greiner, Carbohydrate Res., 327, 147 (2000).
12. N.-S. Li, X.-Q. Tang and J. A. Piccirilli, Organic Letters, 3, 1025 (2001).
13. [a] T. A. Logothetis, U. Eilitz, W. Hiller and K. Burger, Tetrahedron, 54, 14023 (1998);
14. [b] U. Eilitz, C. Böttcher, J. Sieler, S. Gockel, A. Haas and K. Burger, Tetrahedron, 57, 3921 (2001).
15. I. Ruppert, K. Schlich and W. Volbach, Tetrahedron Lett., 25, 2195 (1984).
16. [a] C.E. Ballou, J. Am. Chem. Soc., 79, 165 (1957);
17. [b] R. E. Ireland, L. Courtney and B. J. Fitzsimmons, J. Org. Chem., 48, 5186 (1983).
18. [a] S. Czernecki, C. Georgoulis, C. L. Stevens and K. Vijayakumaran, Tetrhedron Lett., 26, 1699 (1985);
19. [b] R. C. Petter and D. G. Powers, Tetrahedron Lett., 30, 659 (1989);
20. [c] S. Czernecki, A. Ezzitonni and P. Krausz, Synthesis, 651 (1990).
21. [a] D. B. Dess and J. C. Martin, J. Org. Chem., 48, 4156 (1983);
22. [b] R. E. Ireland and L. Liu, J. Org. Chem., 58, 2899 (1993);
23. [c] M. S. Wolfe and R. E. Harry-O'Kuru, Tetrahedron Lett., 36, 7611 (1995).
24. For excellent reviews see: [a] G. K. S. Prakash and A. K. Judin, Chem. Rev. 97, 757 (1997);
25. [b] R. P. Singh and J. M. Shreeve, Tetrahedron, 56, 7613 (2000) and literature cited therein.
26. E. C. Tongco, G. K. S. Prakash and G. A. Olah, Synlett, 1193 (1997).
27. N. Maggiarosa, W. Tyrra, D. Naumann. N. V. Kirij, Y. L. Yagupolskii, Angew. Chem., Int. Ed. Engl., 38, 2252 (1999).
28. R. P. Singh and J. M. Shreeve, J. Org. Chem., 65, 3241 (2000).
29. U. Eilitz, PhD Thesis, University of Leipzig (1999).
30. C. C. Mathews and K. E. van Holde, Biochemistry 2nd. ed., The Benjamin/Cummings Publishing Company, 286 (1996).
31. J. K. Novak and F. Sorm, Collect. Czech. Chem. Commun., 34, 857 (1969).
32. [a] C. Pedersen and H. G. Fletcher, J. Am. Chem. Soc., 82, 945 (1960);
33. [b] A. Hordvik, Acta Chem. Scand., B28, 261 (1974).
34. A. H. Haines and P. R. Rundie, J. Chem. Soc., C 1691 (1970).
35. [a] D. Seebach, Angew. Chem., Int. Ed. Engl., 29, 1320 (1990);
36. [b] M. Hudlicky and A.E. Pavlath, Chemistry of Organic Fluorine Compounds II, ACS Monograph, Am. Chem. Soc., Washington DC (1995).
37. U. Eilitz, C. Böttcher, L. Hennig, C. Boyer, A. Haas, K. Burger, J. Fluorine Chem., 115, 149 (2002).
38. nd ed., VCH Weinheim 257 (1995).
39. [a] W. J. Middleton, J. Org. Chem., 40, 574 (1975);
40. [b] M. Hudlicky, Org. React., 35, 513 (1988);
41. [c] H. Hayakawa, F. Takai, H. Tanaka, T. Miyasaka and K. Yamaguchi, Chem. Pharm. Bull., 38, 1136 (1990).
42. J. Thiem and B. Meyer, Chem. Ber., 113, 305 (1980).
43. G. R. Perdomo and J. J. Kropinsky, Tetrahedron Lett., 28, 5595 (1987).
44. [a] H. Hashimoto, M. Kawa, Y. Saito, T. Date, S. Horito and J. Yoshimura, Tetrahedron Lett., 28, 3505 (1987);
45. [b] B. Classon, P. J. Garegg and B. Samuelson, Acta Chem. Scand. Ser. B, 38, 419 (1984).