Synthesis and conformational behavior of purine and pyrimidine β-D-threo-hex-3'-enopyranosyl nucleosides

Tetrahedron

Volumn 52, Issue 27, 1996, Pages 9249-9262

  Luyten, Ingrid ^a   Herdewijn, Piet ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030184237     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00474-7     Document Type: Article

References (30)

1. 1. Herdewijn, P.; Balzarini, J.; de Clercq, E.; Advances in Antiviral Drug Design. JAI Press. 1993, Vol. 1, pp 233-318.
2. 2. Herdewijn, P.; Van Aerschot, A. Bull. Soc. Chim. Belg. 1990, 99, 895; Herdewijn, P.; Van Aerschot, A.; Balzarini, J.; de Clercq, E.; Nucleosides and Nucleotides 1991, 10, 119.
3. 2. Herdewijn, P.; Van Aerschot, A. Bull. Soc. Chim. Belg. 1990, 99, 895; Herdewijn, P.; Van Aerschot, A.; Balzarini, J.; de Clercq, E.; Nucleosides and Nucleotides 1991, 10, 119.
4. 3. Verheggen, I.; Van Aerschot, A; Toppet, S.; Snoeck, R.; Janssen, G.; Claes, P.; Balzarini, J.; De Clercq, E.; Herdewijn, P.; J. Med Chem. 1993, 36, 2033-2040.
5. 4. Konkel, M.J., Vince, R. Tetrahedron 1996, 52, 799-808.
6. 5. Pérez-Pérez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn, P.; J. Org. Chem. 1995; Harnden, M. R.; Parkin, A.; Parrat, M. J.; Perkins, R. M.; J. Med. Chem. 1993, 36, 1343-1355; Jenny, T. F.; Previsani, N.; Benner, S. A.; Tetrahedron Lett. 1991, 48, 7029-7032; Toyota, A.; Katagiri, N.; Kaneko, C.; Synth. Commun. 1993, 23, 1295-1305; Rodriquez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi J. J.; Jr.; Tetrahedron Lett. 1993, 34, 6233-6236
7. 5. Pérez-Pérez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn, P.; J. Org. Chem. 1995; Harnden, M. R.; Parkin, A.; Parrat, M. J.; Perkins, R. M.; J. Med. Chem. 1993, 36, 1343-1355; Jenny, T. F.; Previsani, N.; Benner, S. A.; Tetrahedron Lett. 1991, 48, 7029-7032; Toyota, A.; Katagiri, N.; Kaneko, C.; Synth. Commun. 1993, 23, 1295-1305; Rodriquez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi J. J.; Jr.; Tetrahedron Lett. 1993, 34, 6233-6236
8. 5. Pérez-Pérez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn, P.; J. Org. Chem. 1995; Harnden, M. R.; Parkin, A.; Parrat, M. J.; Perkins, R. M.; J. Med. Chem. 1993, 36, 1343-1355; Jenny, T. F.; Previsani, N.; Benner, S. A.; Tetrahedron Lett. 1991, 48, 7029-7032; Toyota, A.; Katagiri, N.; Kaneko, C.; Synth. Commun. 1993, 23, 1295-1305; Rodriquez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi J. J.; Jr.; Tetrahedron Lett. 1993, 34, 6233-6236
9. 5. Pérez-Pérez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn, P.; J. Org. Chem. 1995; Harnden, M. R.; Parkin, A.; Parrat, M. J.; Perkins, R. M.; J. Med. Chem. 1993, 36, 1343-1355; Jenny, T. F.; Previsani, N.; Benner, S. A.; Tetrahedron Lett. 1991, 48, 7029-7032; Toyota, A.; Katagiri, N.; Kaneko, C.; Synth. Commun. 1993, 23, 1295-1305; Rodriquez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi J. J.; Jr.; Tetrahedron Lett. 1993, 34, 6233-6236
10. 5. Pérez-Pérez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn, P.; J. Org. Chem. 1995; Harnden, M. R.; Parkin, A.; Parrat, M. J.; Perkins, R. M.; J. Med. Chem. 1993, 36, 1343-1355; Jenny, T. F.; Previsani, N.; Benner, S. A.; Tetrahedron Lett. 1991, 48, 7029-7032; Toyota, A.; Katagiri, N.; Kaneko, C.; Synth. Commun. 1993, 23, 1295-1305; Rodriquez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi J. J.; Jr.; Tetrahedron Lett. 1993, 34, 6233-6236
11. 6. Garegg, P. J.; Samuelson, B., Synthesis, 1979, 469; Liu, Z., Classon, B.; Samuelson, B.; J. Org. Chem. 1990, 55, 4273; Pérez-Pérez, M.-J.; Rozenski, J.; Herdewijn, P.; Bioorg. Med. Chem. Lett. 1994, 4, 1199-1202
12. 6. Garegg, P. J.; Samuelson, B., Synthesis, 1979, 469; Liu, Z., Classon, B.; Samuelson, B.; J. Org. Chem. 1990, 55, 4273; Pérez-Pérez, M.-J.; Rozenski, J.; Herdewijn, P.; Bioorg. Med. Chem. Lett. 1994, 4, 1199-1202
13. 6. Garegg, P. J.; Samuelson, B., Synthesis, 1979, 469; Liu, Z., Classon, B.; Samuelson, B.; J. Org. Chem. 1990, 55, 4273; Pérez-Pérez, M.-J.; Rozenski, J.; Herdewijn, P.; Bioorg. Med. Chem. Lett. 1994, 4, 1199-1202
14. 7. Green, T. W., Wuts, P. G. M. In: Protective Groups in Organic Chemistry, Wiley & Sons, 1991, and references therein.
15. 8. Cruickshank, K. A.; Jiricny, J.; Reese, C. B.; Tetrahedron Lett. 1984, 25, 681-684
16. 9. Bronson, J. J.; Ghazzouli, I.; Hitchcock, M. J. M.; Webb, R. R., II; Martin, J. C.; J. Med. Chem. 1989, 32, 1457-1463.
17. 10. Lin, T.; Nucleic Acid Chem. III; Townsend, Leroy B.; Tipson R. Stuart Eds.; Wiley: New York 1991, 63-66; Krug, A.; Schmidt, S.; Lekschas, J., Lemke, K.; Cech, D.; Journal f. Prakt. Chemie 1989, 331, 835-842
18. 10. Lin, T.; Nucleic Acid Chem. III; Townsend, Leroy B.; Tipson R. Stuart Eds.; Wiley: New York 1991, 63-66; Krug, A.; Schmidt, S.; Lekschas, J., Lemke, K.; Cech, D.; Journal f. Prakt. Chemie 1989, 331, 835-842
19. 11. Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi, J.J. Jr.; Tetrahedron Lett. 1993, 34, 6233-6236
20. 12. Jindrich, J.; Holy, A.; Dvorakova, H.; Collect. Czech. Chem. Commun. 1993, 58, 1645-1667
21. 13. Ness, R. K.; Synthetic procedures in Nucleic Acid Chemistry; Zorbach, W. W. Tipson, R. S., Eds.; John Wiley and Sons: New York, 1968; Vol I, p 185
22. 14. Huang, M.; Secrist III, J.; Montgomery, J.; J. Med. Chem. 1984, 27, 800-802
23. 15. Xsimula is a Laocoon-3 based simulation programm written by B. R. Leeflang used in combination with the triton NMR software package (Bijvoet Center, Utrecht University)
24. 16. Kirby, A. J.; The Anomeric Effect and Related Stereoelectronic Effects of Oxygen; Springer-Verlag: New York, 1983
25. 17. Juaristi, E.; Cuevas, G., Tetrahedron 1992, 48, 5019-5087
26. 18. Zefirov, N. S.; Tetrahedron 1977, 33, 3193-3202
27. 19. Denmark, S. E., Dappen, M. S.; J. Org. Chem. 1984, 49, 798-806
28. 20. Denmark, S. E.; Dappen, M. S.; Sear, N. L.; Jacobs, R. T.; J. Am. Chem. Soc. 1990, 112, 3466-3474
29. 5.
30. 22. Kovacs, L., Bull. Soc. Chim. Fr. 1995, 132, 1015-1019.