Reactivity of 3H-1,2,4-dithiazole-3-thiones and 3H-1,2-dithiole-3-thiones as sulfurizing agents for oligonucleotide synthesis

Tetrahedron Letters

Volumn 52, Issue 3, 2011, Pages 434-437

  Guzaev, Andrei P ^a  

^a AM Chemicals LLC   (United States)

Author keywords

Oligonucleotide synthesis; Phosphoramidite synthesis; Phosphorothioate; Sulfurization

Indexed keywords

3H 1,2 DITHIOLE 3 THIONE; 3H 1,2,4 DITHIAZOLE 3 THIONE; DNA; OLIGONUCLEOTIDE; PHOSPHORAMIDOUS ACID; SULFURTRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; DNA SYNTHESIS; RNA SYNTHESIS; SOLID; STOICHIOMETRY; SYNTHESIS;

EID: 78650235075     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.086     Document Type: Article

References (25)

1. R.P. Iyer, L.R. Phillips, W. Egan, J.B. Regan, and S.L. Beaucage J. Org. Chem. 55 1990 4693 4699
2. H. Vu, and B.L. Hirschbein Tetrahedron Lett. 32 1991 3005 3008
3. H.C.P.F. Roelen, P.C.J. Kamer, H. Van den Elst, G.A. Van der Marel, and J.H. Van Boom Recl. Trav. Chim. Pays-Bas 110 1991 325 331
4. M.V. Rao, C.B. Reese, and Z. Zhao Tetrahedron Lett. 33 1992 4839 4842
5. W.J. Stec, B. Uznanski, A. Wilk, B.L. Hirschbein, K.L. Fearon, and B.J. Bergot Tetrahedron Lett. 33 1993 5317 5320
6. M.V. Rao, and K. Macfarlane Tetrahedron Lett. 35 1994 6741 6744
7. V.A. Efimov, A.L. Kalinkina, O.G. Chakhmakhcheva, T.S. Hill, and K. Jayaraman Nucleic Acids Res. 23 1995 4029 4033
8. L. Chen, T.R. Thompson, R.P. Hammer, and G. Barany J. Org. Chem. 61 1996 6639 6645
9. Q. Xu, K. Musier-Forsyth, R.P. Hammer, and G. Barany Nucleic Acids Res. 24 1996 1602 1607
10. J.-Y. Tang, Y. Han, J.X. Tang, and Z. Zhang Org. Process Res. Dev. 4 2000 194 198
11. J. Hanusek, M.A. Russell, A.P. Laws, P. Jansa, J.H. Atherton, K. Fettes, and M.I. Page Org. Biomol. Chem. 5 2007 478 484
12. Z. Zhang, A. Nichols, J.X. Tang, Y. Han, and J.Y. Tang Tetrahedron Lett. 40 1999 2095 2098
13. Roy, S. K.; Tang, J.-Y. US 6500,944; CA 130:95781.
14. 3: C, 29.25; H, 3.44; N, 20.47; S, 46.85.
15. R.J.S. Beer, N.H. Holmes, and A. Naylor J. Chem. Soc., Perkin Trans. 1 1979 2909 2913
16. K. Gewald J. Prakt. Chem. 31 1966 214 220
17. D.E. Bergstrom, and P.W. Shum J. Org. Chem. 53 1988 3953 3958
18. 3): δ 65.04.
19. 2O): δ 56.65.
20. 2O): δ 56.28.
21. B. Uznanski, W. Niewiarowski, and W.J. Stec Tetrahedron Lett. 23 1982 4289 4292
22. B.V.L. Potter, B.A. Connolly, and F. Eckstein Biochemistry 22 1983 1369 1377
23. OMe stand for the respective 2′-O-methyl-ribonucleotide residues.
24. G. Zon Oligonucleoside Phosphorothioates S. Agrawal, Protocols for Oligonucleotides and Analogs. Synthesis and Properties 1983 Humana Press Totowa, NJ 165 189
25. C.B. Reese, and Q. Song Nucleic Acids Res. 25 1997 2943 2944