Synthesis of carbocyclic pyrimidine nucleosides using the Mitsunobu reaction - Part II: Influence of the solvent on N1- versus O2- alkylation

Synlett

Volumn , Issue 2, 2006, Pages 324-326

  Ludek, Olaf R ^a   Meier, Chris ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Antiviral agents; Carbocyclic nucleosides; Medicinal chemistry; Mitsunobu reaction; Regio selectivity

Indexed keywords

ABACAVIR; ANTIVIRUS AGENT; CARBOCYCLIC PYRIMIDINE NUCLEOSIDE; ENTECAVIR; HETEROCYCLIC COMPOUND; PYRIMIDINE NUCLEOSIDE; SOLVENT; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MITSUNOBU REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 32344433120     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-923580     Document Type: Article

References (22)

1. Ludek, O. R.; Meier, C. Synlett 2005, 3145.
2. Marquez, V. E. In Advances in Antiviral Drug Design, Vol. 2; De Clercq, E., Ed.; JAI Press: Greenwich, 1996, 89-146.
3. Agrofoglio, L. A.; Challand, S. R. Acyclic, Carbocyclic and L-Nucleosides; Kluwer Academic Publishers: Dordrecht, Boston, London, 1998.
4. Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
5. Daluge, S. M.; Martin, M. T.; Sickles, B. R.; Livingston, D. A. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 297.
6. Bisacchi, G. S.; Chao, S. T.; Bachard, C.; Daris, J. P.; Innaimo, S.; Jacobs, G. A.; Kocy, O.; Lapointe, P.; Martel, A.; Merchant, Z.; Slusarchyk, W. A.; Sundeen, J. E.; Young, M. G.; Colonno, R.; Zahler, R. Bioorg. Med. Chem. Lett. 1997, 7, 127.
7. (a) Balzarini, J.; Baumgartner, H.; Bodenteich, M.; De Clercq, E.; Griengl, H. Nucleosides Nucleotides 1989, 8, 855.
8. (b) Wyatt, P. G.; Anslow, A. S.; Coomber, B. A.; Cousins, R. P. C.; Evans, D. N.; Gilbert, V. S.; Humber, D. C.; Paternoster, I. L.; Sollis, S. L.; Tapolczay, D. J.; Weingarten, G. G. Nucleosides Nucleotides 1995, 14, 2039.
9. (a) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
10. (b) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
11. (c) Crimmins, M. T. Tetrahedron 1998, 54, 9229.
12. (a) Jenny, T. F.; Previsani, N.; Benner, S. A. Tetrahedron Lett. 1991, 32, 7029.
13. (b) Jenny, T. F.; Horlacher, J.; Previsani, N.; Benner, S. A. Helv. Chim. Acta 1992, 75, 1944.
14. (c) Bonnal, C.; Chavis, C.; Lucas, M. J. Chem. Soc., Perkin Trans. 1 1994, 1401.
15. (d) Pérez-Pérez, M. J.; Rozenski, J.; Busson, R.; Herdewijn, P. J. Org. Chem. 1995, 60, 1531.
16. (e) Borthwick, A. D.; Crame, A. J.; Exall, A. M.; Weingarten, G. G.; Mahmoudian, M. Tetrahedron Lett. 1995, 36, 6929.
17. (f) Schmitt, L.; Caperelli, C. A. Nucleosides Nucleotides 1997, 16, 2165.
18. (g) Choo, H.; Chong, Y.; Chu, C. K. Org. Lett. 2001, 3, 1471.
19. (a) Ludek, O. R.; Meier, C. Synthesis 2003, 13, 2101.
20. (b) Ludek, O. R.; Balzarini, J.; Meier, C. Eur. J. Org. Chem. 2005, in press.
21. Cruickshank, K. A.; Jiricny, J.; Reese, C. B. Tetrahedron Lett. 1984, 25, 681.
22. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd Ed.; VCH-Verlagsgesellschaft GmbH: Weinheim, 1988.