Solid-phase synthesis of dinucleoside and nucleoside-carbohydrate phosphodiesters and thiophosphodiesters

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6693-6696

  Ahmadibeni, Yousef ^a   Parang, Keykavous ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DINUCLEOSIDE; MONOSUBSTITUTION; NUCLEOSIDE-CARBOHYDRATE PHOSPHODIESTERS; SULFURIZATION; THIOPHOSPHODIESTERS;

CARBOHYDRATES; DERIVATIVES; ETHYLENE; POLYMERS; SUBSTITUTION REACTIONS; SULFUR; SYNTHESIS (CHEMICAL);

ESTERS;

BEAUCAGE REAGENT; CARBOHYDRATE; N,N DIISOPROPYLAMINO 1,3,2 OXATHIAPHOSPHOLANE; NUCLEOSIDE; POLYMER; REAGENT; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; OXIDATION; PHASE TRANSITION; REACTION ANALYSIS; RING OPENING; SOLID; SYNTHESIS;

CARBOHYDRATES; ESTERS; MOLECULAR STRUCTURE; NUCLEOSIDES; PHOSPHORUS; SULFHYDRYL COMPOUNDS;

EID: 33747400883     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0611115     Document Type: Article

References (31)

1. Kondo, N. S.; Fang, K. N.; Miller, P. S., Ts'o, P. O. P. Biochemistry 1972, 11, 1991-2003.
2. Puech, F.; Gosselin, G.; Balzarini, J.; De Clercq, E.; Imbach, J.-L. J. Med. Chem. 1988, 31, 1897-1907.
3. Henin, Y.; Gouyette, C.; Schwartz, O.; Debouzy, J.-C.; Neumann, J.-M.; Huynh-Dinh, T. J. Med. Chem. 1991, 34, 1830-1837.
4. Desseaux, C.; Gouyette, C.; Henin, Y.; Huynh-Dinh, T. Tetrahedron 1995, 51, 6739-6756.
5. Namane, A.; Gouyette, C.; Fillion, M.-P.; Fillion, G.; Huynh-Dinh, T. J. Med. Chem. 1992, 35, 3039-3044.
6. Montgomery, J. A.; Thomas, H. J. J. Med. Chem. 1967, 10, 1163.
7. Gouyette, C.; Neumann, J. M.; Fauve, R.; Huynh-Dinh, T. Tetrahedron Lett. 1989, 30, 6019-6022.
8. Eckstein, F. Antisense Nucleic Acid Drug Dev. 2000, 10, 117-121.
9. Eckstein, F. Annu. Rev. Biochem. 1985, 54, 367-402.
10. Eckstein, F. J. Am. Chem. Soc. 1966, 88, 4292-4294.
11. Ravikumar, V. T.; Kumar, R. K.; Capaldi, D. C.; Turney, B.; Rentel, C.; Cole, D. L. Org. Process Res. Dev. 2003, 7, 259-266.
12. Yang, X.; Bassett, S. E.; Li, X.; Luxon, B. A.; Herzog, N. K.; Shope, R. E.; Aronson, J.; Prow, T. W.; Leary, J. F.; Kirby, R.; Ellington, A. D.; Gorenstein, D. G. Nucleic Acids Res. 2002, 30, e132, 1-8.
13. Parang, K.; Wiebe, L. I.; Knaus, E. E. Curr. Med. Chem. 2000, 7, 995-1039.
14. Van Rompay, A. R.; Johansson, M.; Karlsson, A. Pharmacol. Ther. 2000, 87, 189-198.
15. Xiao, Q.; Ju, Y.; Zhao, Y. Synth. Commun. 2003, 33, 4157-4162.
16. Robinson, W. E., Jr.; Montefiori, D. C.; Mitchell, W. M. AIDS Res. Hum. Retroviruses 1987, 3, 265-282.
17. Debouzy, J. C.; Herve, M.; Neumann, J. M.; Gouyette, C.; Dupraz, B.; Huynh-Dinh, T. Biochem. Pharmacol. 1990, 39, 1657-1664.
18. Neumann, J. M.; Herve, M.; Debouzy, J.-C.; Guerra, F. I.; Gouyette, C.; Dupraz, B.; Huynh-Dinh, T. J. Am. Chem. Soc. 1989, 111, 4270-4277.
19. Desseaux, C.; Huynh-Dinh, T. Bioorg. Med. Chem. Lett. 1993, 3, 1547-1550.
20. Baraniak, J.; Kaczmarek, R.; Stec, W. J. Tetrahedron Lett. 2000, 41, 9139-9142.
21. Okruszec, A.; Sierzchala, A.; Fearon, K. L.; Stec, W. J. J. Org. Chem. 1995, 60, 6998-7005.
22. Okruszek, A.; Olesiak, M.; Balzarini, J. J. Med. Chem. 1994, 37, 3850-3854.
23. Okruszek, A.; Olesiak, M.; Krajewska, D.; Stec, W. J. J. Org. Chem. 1997, 62, 2269-2272.
24. Misiura, K.; Szymanowicz, D.; Stec, W. J. Org. Lett. 2005, 7, 2217-2220.
25. Guga, P.; Maciaszek, A.; Stec, W. J. Org. Lett. 2005, 7, 3901-3904.
26. Misiura, K.; Szymanowicz, D.; Stec, W. J. Org. Lett. 2005, 7, 2217-2220.
27. Misiura, K.; Stec, W. J. Synlett 2004, 12, 2143-2146.
28. Guga, P.; Okruszek, G.; Stec, W. J. In Topics in Current Chemistry; Majoral, J. P., Ed.; Springer-Verlag: Berlin Heidelberg, 2002; Vol. 220, pp 169-200.
29. Guga, P.; Stec, W. J. In Current Protocols in Nucleic Acid Chemistry; Beaucage, S. L., Bergstrom, D. E., Click, G. D., Jones, R. A., Eds.; John Wiley & Sons: Hoboken, 2003; pp 4.17.1-4.17.28.
30. Ahmadibeni, Y.; Parang, K. Org. Lett. 2005, 7, 1955-1958.
31. Iyer, R. P.; Egan, W.; Regan, J. B.; Beaucage, S. L. J. Am. Chem. Soc. 1990, 112, 1253-1254.