Synthesis of 3′-C-substituted thymidine derivatives by free-radical techniques: scope and limitations

Carbohydrate Research

Volumn 342, Issue 2, 2007, Pages 259-267

  Horton, Derek ^a   Chen, Kuangmin ^a   No, Zaesung ^a   Lee, Howard C ^a  

^a AMERICAN UNIVERSITY   (United States)

Author keywords

C Alkylation; Free radical; Nucleoside; Thionoamide; Thionoester; Thymidine

Indexed keywords

C-ALKYLATION; NUCLEOSIDE; THIONOAMIDE; THIONOESTER; THYMIDINE;

ALKYLATION; ESTERS; FREE RADICALS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

NUCLEIC ACIDS;

1 [2,3 DIDEOXY 3 C (2 METHOXYCARBONYLETHYL) BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 1 [5 O (TERT BUTYLDIMETHYLSILYL) 2 DEOXY 3 O [(IMIDAZOLYL)THIOCARBONYL] BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 1 [5 O (TERT BUTYLDIMETHYLSILYL) 2 DEOXY 3 O [(METHYLTHIO)THIOCARBONYL] BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 1 [5 O (TERT BUTYLDIMETHYLSILYL) 2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 1 [5 O (TERT BUTYLDIMETHYLSILYL) 3 C (2 CYANOETHYL) 2,3 DIDEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 1 [5 O (TERT BUTYLDIPHENYLSILYL) 2 DEOXY 3 O [(IMIDAZOLYL)THIOCARBONYL] BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 1 [5 O (TERT BUTYLDIPHENYLSILYL) 2 DEOXY 3 O [(METHYLTHIO)THIOCARBONYL] BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 1 [5 O (TERT BUTYLDIPHENYLSILYL) 2 DEOXY 3 O [(PENTAFLUOROPHENOXY) THIOCARBONYL] BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 1 [5 O (TERT BUTYLDIPHENYLSILYL) 2 DEOXY 3 O [(PHENOXY)THIOCARBONYL] BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 1 [5 O (TERT BUTYLDIPHENYLSILYL) 2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 3 C ALLYL 1 [5 O (TERT BUTYLDIPHENYLSILYL) 2,3 DIDEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL]THYMINE; 5' [2 (TERT BUTYLDIMETHYLSILYL)THYMIDINE]; ACRYLIC ACID METHYL ESTER; ACRYLONITRILE; ALLYLTRIBUTYLTIN; BUTYLTIN DERIVATIVE; CARBONYL DERIVATIVE; FREE RADICAL; PYRIMIDINE NUCLEOSIDE; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG; THIOAMIDE; THYMIDINE;

ARTICLE; DEOXYGENATION; DRUG SYNTHESIS; PRIORITY JOURNAL; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

FREE RADICALS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PYRIMIDINE NUCLEOSIDES; THIOAMIDES; THYMIDINE;

EID: 33846117527     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2006.11.015     Document Type: Article

References (32)

1. Simons C. Nucleoside Mimetics (2001), Gordon & Breach Scientific Chapter 1
2. Vejcik, S. M.; Horton, D. Carbohydr. Res., in press; doi:10.1016/j.carres.2006.12.003.
3. Norris P., Horton D., and Levine B.R. Heterocycles 43 (1996) 2643-2655
4. Blieszner K.C., Horton D., and Markovs R.A. Nucleic Acid Chemistry: New and/or Improved Synthetic Procedures, Methods, and Techniques. Part 3 (1986), Wiley pp 135-139
5. Horton D., and Liu C.-M. Carbohydr. Res. 109 (1982) 282-289
6. Horton D., and Liu C.-M. Carbohydr. Res. 107 (1982) 55-70
7. Horton D., and Markovs R.A. Carbohydr. Res. 80 (1980) 356-363
8. Horton D., and Kokrady S.S. Carbohydr. Res. 80 (1980) 364-374
9. Blieszner K.C., Horton D., and Markovs R.A. Carbohydr. Res. 80 (1980) 24l-262
10. Horton D., and Markovs R.A. Carbohydr. Res. 80 (1980) 262-275
11. Wolfrom M.L., Garg H.G., and Horton D. J. Org. Chem. 30 (1965) 1556-1560
12. Sarafianos S.G., Hughes S.H., and Arnold E. Int. J. Biochem. Cell Biol. 36 (2004) 1706-1715
13. De Clercq E. Nature Rev. Drug Discovery 1 (2002) 13-25
14. For preliminary reports, see: Lee, H. C., Chen, K., No, Z., Horton, D., Abstr. Pap., 20th Int. Carbohydr. Symp., Hamburg, Germany, August 27-September 1, 2000, Abstr. B-160; Abstr. Pap. Am. Chem. Soc. Meet. 2000, 220, CARB-76 (2000), Washington, DC, August 20-24, 2000.
15. Herdewijn P., Balzarini L., De Clercq E., Pauwels R., Baba M., Broder S., and Vanderhaeghe H. J. Med. Chem. 30 (1987) 1270-1278
16. Sahlberg C. Tetrahedron Lett. 33 (1992) 679-682
17. Chu C.K., Doboszewski B., Schmidt W., Ullas G.V., and Van Roey P. J. Org. Chem. 54 (1989) 2767-2769
18. Fiandor J., and Tam S.Y. Tetrahedron Lett. 31 (1990) 597-600
19. De Mesmaeker A.D., Lebreton J., Waldner A., Fristsch V., Wolf R.M., and Freier S.M. Synlett (1993) 733-736
20. Ogilvie K.K. Can. J. Chem. 51 (1973) 3799-3807
21. Sanghvi Y.S., Bharadwaj R., Debart F., and De Mesmaeker A.D. Synthesis (1994) 1163-1166
22. Keck G., and Yates J.B. J. Am. Chem. Soc. 104 (1982) 5829-5831
23. Giese B., Dupuis J., Leising M., Nix M., and Lindner H.J. Carbohydr. Res. 171 (1987) 329-341
24. Ogilvie K.K., and Iwacha D.J. Tetrahedron Lett. (1973) 317-319
25. No, Z. Ph.D. Dissertation, Ohio State University, 1990; Dissertation Abstr. Int. 1991, 51, 5876.
26. Matulie-Adamie J., and Watananbe K.A. J. Chem. Soc., Chem. Commun. (1985) 1535
27. Keck G.E., Enholm E.J., Yates J.B., and Wiley M.R. Tetrahedron 41 (1985) 4079-4094
28. Chen, K. Ph.D. Dissertation, Ohio State University, 1996; Dissertation Abstr. Int. 1997, 57, 4393.
29. Lin T.S., Zhu J.L., Dutschman G.E., Cheng Y.C., and Prusoff W.H. J. Med. Chem. 36 (1993) 353-362
30. Svansson L., Kvarnström I., Classon B., and Samuelsson B. J. Org. Chem. 56 (1991) 2993-2997
31. Gordon A.J., and Ford R.A. The Chemist's Companion (1972), John Wiley & Sons p 379
32. Julien, P. H.; Moffatt, J. G. US Patent 3,282,941, 1964.