Efficient synthesis of 5-(thioalkyl)uridines via ring opening of α-ureidomethylene thiolactones

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5708-5709

  Sun, Sengen ^a   Tang, Xiao Qing ^a   Merchant, Aziz ^a   Anjaneyulu, P S R ^a   Piccirilli, Joseph A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

URIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029800555     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960966m     Document Type: Article

References (27)

1. (a) Ferentz, A. E.; Verdine, G. L. Nucleic Acids Mol. Biol. 1994, 8, 14.
2. (b) Chaudhuri, N. C.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 10434.
3. (c) Wang, H.; Osborne, S. E.; Zuiderweg, E. R. P.; Glick, G. D. J. Am. Chem. Soc. 1994, 116, 5021.
4. Stanojevic, D.; Verdine, G. L. Nature Struct. Biol. 1995, 2, 450.
5. (a) Goodwill, J. T.; Glick, G. D. Tetrahedron Lett. 1994, 35, 1647.
6. (b) Sigurdsson, S. T.; Tuschl, T.; Eckstein, F. RNA 1995, 1, 575.
7. (c) Allerson, C. R.; Verdine, G. L. Chem. Biol. 1995, 2, 667.
8. (d) Gao, H.; Yang, M.; Patel R.; Cook, A. F. Nucleic Acids Res. 1995, 23, 2025.
9. (a) Careaga, C. L.; Sutherland, J.; Sabeti, J.; Falke, J. J. Biochemistry 1995, 34, 3048.
10. (b) Creighton, T. E. Prog. Biophys. Mol. Biol. 1978, 33, 231.
11. (c) Creighton, T. E. Biochem. J. 1990, 270, 1.
12. (d) Weissman, J. S.; Kim, P. S. Science 1991, 253, 1368.
13. Hillen, W.; Egert, E.; Lindner, H. J.; Gassen, H. G. Biochemistry 1978, 17, 5314.
14. Goodwin, J. T.; Glick, G. D. Tetrahedron Lett. 1993, 34, 5549.
15. (a) Niedballa, U.; Vorbruggen, H. J. Org. Chem. 1974, 39, 3654, 3664, 3668, 3672;
16. (b) 1976, 41, 2084.
17. (c) Vorbruggen, H.; Hofle, G. Chem. Ber. 1981, 114, 1256.
18. (a) Denny, G. H.; Ryder, M. A. J. Med. Chem. 1974, 17, 1230.
19. (b) Fissekis, J. D.; Sweet, F. J. Org. Chem. 1973, 28, 264.
20. Cosstick, R.; Vyle, J. S. Nucl. Acids Res. 1990, 18, 829.
21. Korte, F.; Lohmer, K. H. Chem. Ber. 1958, 91, 1397.
22. Overberger, C. G.; Weise, J. K. J. Am. Chem. Soc. 1968, 90, 3533.
23. Korte, F.; Buchel, K. H. Chem. Ber. 1960, 93, 1021.
24. Wunsch, E.; Moroder, L.; Romani, S. Physiol. Chem. 1982, 363, 1463.
25. Hakimelahi, G. H.; Proba, Z. A.; Ogilvie, K. K. Can. J. Chem. 1982, 60, 1106.
26. Usman, N.; Ogilvie, K. K.; Jiang, M.-Y.; Cedergren, R. J. J. Am. Chem. Soc. 1987, 109, 7845.
27. Divakar, K. J.; Mottoh, A.; Reese, C. B.; Sanghvi, Y. S. J. Chem. Soc., Perkin Trans. 1 1990, 969.