Synthesis of 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine (d4t; stavudine) from 5-methyluridine

Nucleosides and Nucleotides

Volumn 15, Issue 1-3, 1996, Pages 47-58

  Shiragami, Hiroshi ^a   Ineyama, Takashi ^a   Uchida, Yumiko ^a   Izawa, Kunisuke ^a  

^a AJINOMOTO CO INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

STAVUDINE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029983764     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319608002369     Document Type: Article

References (40)

1. Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St. Clair, M. H.; Lehrman, S. N.; Gallo, R. C.; Bolognesi, D.; Barry, D. W.; Broder, S. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7096.
2. (a) Mitsuya, H.; Broder, S. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 1911.
3. (b) Dahlberg, J. E.; Mitsuya, H.; Blam, S. B.; Broder, S.; Aaronson, S. A. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 2469.
4. (c) Kim, C.; Marquez, V. E.; Broder, S.; Mitsuya, H.; Driscoll, J. S. J. Med. Chem. 1987, 30, 862.
5. (d) Herdewijn, P.; Balzarini, J.; De Clercq, E.; Pauwels, R.; Baba, M; Broder, S. J. Med. Chem. 1987, 30, 1270.
6. (a) Cooney, D. A.; Dalal, M.; Mitsuya, H.; McMahon, J. B.; Nadkarni, M.; Balzarini, J.; Broder, S.; Johns, D. G. Biochem. Pharmacol. 1986, 35, 2065.
7. (b) Lin, T. S.; Chen, M. S.; McLaren, C.; Gao, Y. S.; Ghazzouli, I.; Prusoff, W. H. J. Med. Chem. 1987, 30, 440.
8. Human immunodeficiency virus, which causes AIDS. For instance (a) Provic, M; Sarngadharan, M. G.; Read, E.; Gallo, R. C. Science (Washington, D. C.) 1984, 224, 497. (b) Broder, S.; Gallo, R. C. Annu. Rev. Immunol. 1985, 3, 321. (c) Wong-Staal, F.; Gallo, R. C. Nature (London), 1985, 317, 395.
9. Human immunodeficiency virus, which causes AIDS. For instance (a) Provic, M; Sarngadharan, M. G.; Read, E.; Gallo, R. C. Science (Washington, D. C.) 1984, 224, 497. (b) Broder, S.; Gallo, R. C. Annu. Rev. Immunol. 1985, 3, 321. (c) Wong-Staal, F.; Gallo, R. C. Nature (London), 1985, 317, 395.
10. Human immunodeficiency virus, which causes AIDS. For instance (a) Provic, M; Sarngadharan, M. G.; Read, E.; Gallo, R. C. Science (Washington, D. C.) 1984, 224, 497. (b) Broder, S.; Gallo, R. C. Annu. Rev. Immunol. 1985, 3, 321. (c) Wong-Staal, F.; Gallo, R. C. Nature (London), 1985, 317, 395.
11. (a) Broder, S. Med. Res. Rev. 1990, 10, 410.
12. (b) Johnson, V. A.; Barlow, M. A.; Merrill, D. P.; Chou, T-C.; Hirsch, M. S. J. Infect. Dis. 1990, 161, 1059.
13. (c) Dornsife, R. A.; St Clair, M. H.; Huang, A. Averett, D. R. Antimicrob. Agents Chemother. 1990, 35, 322.
14. (d) Baba, M.; Pauwels, R.; Herdewijn, P.; De Clercq, E.; Desmyter, J.; Vandeputte, M. Biochem. Biophis. Res. Commun. 1987, 142, 128.
15. (e) Hamamoto, Y.; Nakashima, H.; Matsui, T.; Matsuda, A.; Ueda, T.; Yamamoto, N. Antimicrob. Agents Chemother. 1987, 31, 907.
16. (f) Lin, T. S.; Schinazi, R. F.; Prusoff, W. H. Biochem. Pharmacol. 1987, 36, 2713.
17. (a) Horwitz, J. P.; Chua, J.; Noel, M.; Donatti, J. T. J. Org. Chem. 1967, 32, 817.
18. (b) Martin, J. C.; Mansuri, M. M.; Starrett, J. E., Jr.; Sommadossi, J-P.; Brankovan, V.; Ghazzouli, I.; Ho, H-T.; Hitchcock, M. J. M. Nucleosides & Nucleotides 1989, 8, 841.
19. (c) Mansuri, M. M.; Starrett, J. E., Jr.; Ghazzouli, I.; Hitchcock, M. J. M.; Sterzycki, R. Z.; Brankovan, V.; Lin, T-S.; August, E. M.; Prusoff, W. H.; Sommadossi, J-P.; Martin, J. C. J. Med. Chem. 1989, 32, 461.
20. Vial, J. M.; Agback, P.; Chattopadhyaya, J. Nucleosides & Nucleotides 1990, 9, 245.
21. (a) Joshi, B. V.; Rao, T. S.; Reese, C. B. J. Chem. Soc. Perkin Trans. 1 1992, 2537.
22. (b) Cosford, N. D. P.; Schinazi, R. F. Nucleoside & Nucleotides 1993, 12, 149.
23. Negrón, G.; Islas, G.; Díaz, Y.; Cruz, R.; Quiclet-Sire, B. Nucleosides & Nucleotides 1994, 13, 1011.
24. (a) Ishii, M.; Shirae, H.; Yokozeki, K. Agric. Biol. Chem. 1989, 53, 3209.
25. (b) Shirae, H.; Ishii, M.; Yokozeki, K. Jpn. Kokai Tokkyo Koho JP 90-23882.
26. (c) Maruyama, S.; Kumon, T. Jpn. Kokai Tokkyo Koho JP 94-128280.
27. (a) Shimizu, A.; Yamada, H. Hakko to Kogyo 1983, 41, 460.
28. (b) Yamada, H.; Shimizu, A. "Ullman's Encyclopedia of Industrial Chemistry" Vol. A4, VCH Verlagsgesellschaft 1985, 150.
29. (c) Shimizu, A.; Yamada, H. kagaku to Seibutsu 1986, 24, 452.
30. (d) Yamada, H.; Shimizu, A. Angew. Chem. Int. Ed. Engl. 1988, 27, 622.
31. (a) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P.; J. Org. Chem. 1989, 54, 2217.
32. (b) Mansuri, M. M.; Starrett J. E., Jr.; Wos, J. A.; Tortolani, D. R.; Brodfuehrer, P. R.; Howell, H. G.; Martin, J. C. J. Org. Chem. 1989, 54, 4780.
33. (c) Luzzio, F. A.; Menes, M. E. J. Org. Chem. 1994, 59, 7267.
34. Marumoto, R.; Honjo, M. Chem. Pharm. Bull. 1974, 22, 128.
35. Huang, H.; Chu, C. K. Synth. Commun. 1990, 20, 1039.
36. Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367.
37. Amino Y.; and Iwagami, H. Chem. Pharm, Bull. 1991, 39, 622.
38. (a) Norman, D. G.; Reese, C. B. Synthesis 1983, 304.
39. (b) Shiragami, H.; Tanaka, Y.; Uchida, Y.; Iwagami, H.; Izawa, K.; Yukawa, T. Nucleosides & Nucleotides 1992, 11, 391.
40. Fox, J. J.; Yung, N.; Davoll, J.; Brown, G. B. J. Amer. Chem. Soc. 1956, 78, 2117.