Free radical chain reactions for the preparation of novel anomeric carbohydrate difluoromethylene -phosphonates and -phosphonothioates

Tetrahedron

Volumn 53, Issue 44, 1997, Pages 15085-15100

  Herpin, Timothée F ^a   Motherwell, William B ^a   Roberts, Brian P ^a   Roland, Sylvain ^a   Weibel, Jean Marc ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CONFORMATION; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030826903     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10007-2     Document Type: Article

References (43)

1. a) Eckstein, F. J. Am. Chem. Soc. 1970, 92, 4718.
2. b) Usher, D. A.; Erenrich, E. S.; Eckstein, F. Proc. Nat. Acad. Sci. USA 1972, 69, 115.
3. c) Eckstein, F. Angew. Chem. Int. Ed. Eng. 1983, 22, 423.
4. a) Rothermel, J. D.; Stec, W. J.; Baraniak, J.; Jarstoff, B.; Botelho, L. H. P. J. Biol. Chem. 1983, 258, 12125.
5. b) De Wit, R. J. W.; Hekstra, D.; Jarstoff, B.; Stec, W. J.; Van Haastert, P. J. M.; Van Driel, R.; Jarstoff, B.; Baraniak, J.; Stec, M. W.; Averill, B. A.; Knowles, J. R. J. Am; Chem. Soc. 1993, 115, 2974.
6. a) Eckstein, F. Ann. Rev. Biochem. 1985, 54, 367.
7. b) Matsukura, M.; Sinozuka, K.; Zon, G.; Mitsuya, H.; Reitz, M.; Cohen, J., S.; Broder, S. Proc. Nat. Acad. Sci. USA 1987, 84, 7706.
8. Matsukura, M.; Zon, G.; Sinozuka, K.; Robert-Guroff, M.; Shimada, T.; Stein, C. A.; Wong-Stall, F.; Mitsuya, Cohen, J., S.; Broder, S. Proc. Nat. Acad. Sci. USA 1987, 86, 4244.
9. a) Blackburn, G. M.; Kent, D. E.; Kohlman, F. J. Chem. Soc., Perkin Trans., 1984, 1119.
10. b) Blackburn, G. M.; Eckstein, F.; Kent, D. E.; Perrée, T. D. Nucleosides and Nucleotides, 1985, 4, 165.
11. c) Hebel, D.; Kirk, K. L.; Kinjo, J.; Kovac's, T.; Lesjak, K.; Balzarini, J.; De Clercq, E.; Torrence, P. F. Bioorg. Med. Chem. Lett. 1991, 1, 357.
12. d) Chambers, R. D.; Jaouhari, R.; O'Hagan, J. J. Chem. Soc. Chem. Comm. 1988, 1169.
13. e) Chambers, R. D.; Jaouhari, R.; O'Hagan, J. Tetrahedron, 1989, 45, 5101.
14. f) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763.
15. g) Thatcher, G. R. J.; Campbell, A. S. J. Org. Chem. 1993, 58, 2272.
16. Piettre, S.; Raboisson, P. Tetrahedron Lett., 1996, 37, 2229.
17. a) Motherwell, W. B.; Tozer, M. J.; Ross, B. C. Synlett, 1989, 68.
18. b) Herpin, T. F.; Motherwell, W. B.; Tozer, M. J. Tetrahedron : Asymmetry, 1994, 5, 2269.
19. Herpin, T. F.; Houlton, J. S.; Motherwell, W. B.; Roberts, B. P.; Weibel, J.-M. J. Chem. Soc. Chem. Commun., 1996, 613 and references herein.
20. Martin, S. F.; Dean, D. W.; Wagman, A. S. Tetrahedron Lett., 1992, 33, 1839.
21. Berkowitz, D. B.; Eggen, M.; Shen, Q.; Sloss, D. J. Org. Chem., 1993, 58, 6174.
22. Burton, D. J.; Shin-Ya, S.; Takei, R. J. Fluorine Chem., 1981,18, 197.
23. a) Blackburn, G. M.; Jakeman, D. L.; Ivory, A. J.; Williamson, M. P. Bioorg. and Med. Chem. Lett., 1994, 4, 2573.
24. b) Burton, D. J.; Sprague, L. G. J. Org. Chem., 1988, 53, 1523.
25. c) Burton, D. J.; Sprague, L. G. J. Org. Chem., 1989, 54, 613.
26. a) Lequeux, T. P.; Percy, J. M. Synlett, 1995, 361.
27. b) Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun., 1995, 2111.
28. Smyth, M. S.; Burke Jr., T. R. Tetrahedron Lett., 1994, 35, 551.
29. a) Yang, Z.-Y.; Burton, D. J. Tetrahedron Lett., 1991, 32, 1019.
30. b) Yang, Z.-Y.; Burton, D. J. J. Org. Chem., 1992, 57, 4676.
31. c) Hu, C.-M.; Chen, J. J. Chem. Soc., Perkin Trans, 1, 1993, 327.
32. cMillan, New York, 1964.
33. Piettre, R. Tetrahedron Lett., 1996, 37, 4707.
34. Piettre, R. Tetrahedron Lett., 1996, 37, 2233.
35. Petragnani, N.; Toscano, V. G.; Moura Campos, M. Chem. Ber., 1968, 101, 3070.
36. Giese, B. Angew. Chem., Int. Ed. Engl., 1989, 28, 969.
37. Diethyl thiophosphite was obtained in 85% yield in refluxing toluene for 5 min. In our modified procedure, dibenzyl thiophosphite was obtained in 60% yield by heating the solution for 2h at 95°C. Our attempts to synthesise di-tert-butyl thiophosphite even at a lower temperature only led to decomposition of the starting di-tert-butyl phosphite.
38. a) Barton, D. R. H.; Gero, S. D.; Quiclet-Sire, B.; Samaldi, M. Tetrahedron: Asymmetry, 1994, 5, 2123.
39. b) Giese, B. Angew. Chem., Int. Ed. Engl., 1989, 28, 969.
40. Davies, A. G.; Griller, D.; Roberts, B. P. J. Am. Chem. Soc., 1972, 94, 1782.
41. Neil, I. G.; Roberts, B. P. J. Organomet. Chem., 1975,102, C17.
42. Roberts, B. P.; Singh, K. J. Organomet. Chem., 1978, 159, 31.
43. Houlton, S. J.; Motherwell, W. B.; Ross, B. C.; Tozer, M. J.; Williams, D. J.; Slawin, A. M. Z. Tetrahedron, 1993, 49, 8087.