New protected protecting groups for the 5′-hydroxy group of deoxynucleosides by use of 2-(hydroxymethyl)- and 2-[(methylamino)methyl]benzoyl skeletons and oxidatively cleavable tritylthio and (4-methoxytrityl)thio groups

Helvetica Chimica Acta

Volumn 87, Issue 9, 2004, Pages 2318-2333

  Seio, Kohji ^a,b   Utagawa, Eri ^a,b   Sekine, Mitsuo ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; AROMATIC HYDROCARBONS; HYDROLYSIS; OXIDATION; SYNTHESIS (CHEMICAL);

DEOXYNUCLEOSIDES; INTRAMOLECULAR CYCLIZATION;

SULFUR COMPOUNDS;

(4 METHOXYTRITYL)THIO DERIVATIVE; 2 (HYDROXYMETHYL)BENZOYL DERIVATIVE; 2 [(METHYLAMINO)METHYL]BENZOYL DERIVATIVE; 2 [[(TRITYLTHIO)OXY]METHYL]BENZOYL; 2 [[[(4 METHOXYTRITYL)THIO]METHYLAMINO]METHYL]BENZOYL; 2 [[[(4 METHOXYTRITYL)THIO]OXY]METHYL]BENZOYL; 2 [[METHYL(TRITYLTHIO)AMINO]METHYL]BENZOYL; 2,4 DINITROPHENOL; DNA; HYDROXYL GROUP; NUCLEOSIDE DERIVATIVE; OLIGODEOXYNUCLEOTIDE; SULFENAMIDE DERIVATIVE; TETRATHYMIDYLATE; THYMIDINE DERIVATIVE; TRITHYLTHIO DERIVATIVE; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DNA SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 5644224477     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200490207     Document Type: Article

References (41)

1. A. B. Sierzchala, C. J. Dellinger, J. R. Betley, T. K. Wyrzykiewicz, C. M. Yamada, M. H. Caruthers, J. Am. Chem. Soc. 2003, 125, 13427.
2. K. Seio, M. Sekine, Tetrahedron Lett. 2001, 42, 8657.
3. M. Septak, Nucleic Acids Res. 1996, 24, 3053.
4. J. C. Schulhof, D. Molko, R. Teoule, Nucleic Acids Res. 1987, 15, 397.
5. A. Kume, R. Iwase, M. Sekine, T. Hata, Nucleic Acids Res. 1984, 12, 8525.
6. B. C. Froehler, M. D. Matteuci, Nucleic Acids Res. 1983, 11, 8031.
7. H. Takaku, K. Imai, M. Nagai, Chem. Lett. 1988, 857.
8. G. W. Grams, R. L. Letsinger, J. Org. Chem. 1968, 33, 2589.
9. C. Christodoulou, S. Agrawal, M. J. Gait, Nucleosides Nucleotides 1987, 6, 341.
10. C. M. Dreef-Tromp, E. M. A. van Dam, H. van den Elst, G. A. van der Marel, J. H. van Boom, Nucleic Acids Res. 1990, 18, 6491.
11. C. M. Dreef-Tromp, C. M. Hoogerhout, G. A. van der Marel, J. H. van Boom, Tetrahedron Lett. 1990, 31, 427.
12. T. W. Green, P. G. M. Wuts, 'Protective Groups in Organic Synthesis', 3rd edn., John Wiley & Sons, New York, 1999.
13. J. M. Brown, C. Christodoulou, C. B. Reese, G. J. Sindona, J. Chem. Soc., Perkin Trans. 1 1984, 1785.
14. K. Kamaike, H. Takahashi, K. Morohoshi, N. Kataoka, T. Kakinuma, Y. Ishido, Acta Biochim. Pol. 1998, 45, 949.
15. C. Christodoulou, S. Agrawal, M. J. Gait, in 'Biophosphates and Their Analogues - Synthesis, Structure, Metabolism and Activity', Eds. K. S. Bruzik, W. J. Stec, Elsevier Science, Amsterdam, 1987, p. 9.
16. B. P. Branchaud, J. Org Chem. 1983, 48, 3538.
17. B. P. Branchaud, J. Org. Chem. 1983, 48, 3531.
18. K. Seio, M. Sekine, J. Chem. Soc., Perkin Trans. 1 1993, 3087.
19. K. Alvarez, I. Tworkowski, J.-J. Vasseur, J.-L. Imbach, B. Rayner, Nucleosides Nucleotides 1998, 17, 365.
20. M. Ueki, M. Honda, Y. Kazama, T. Katoh, Synthesis 1994, 21.
21. H. Bazin, J. Heikkilä, J. Chattopadhyaya, Acta. Chem. Scand. B 1985, 39, 391.
22. L. Zervas, D. Borovas, E. Gazis, J. Am. Chem. Soc. 1963, 85, 3660.
23. R. F. Bayfield, E. R. Cole, Phosphorus, Sulfur, Silicon 1989, 45, 237.
24. I. A. Belousova, V. A. Savelova, Y. S. Simanenko, B. V. Panchenko, Russ. J. Org. Chem. 1996, 38, 111.
25. Y. Mizuno, T. Endo, J. Org. Chem. 1978, 43, 684.
26. T. Wada, A. Ohkubo, A. Mochizuki, M. Sekine, Tetrahedron Lett. 2001, 42, 1069.
27. V. Dourtoglou, J.-C. Ziegler, B. Gross, Tetrahedron Lett. 1978, 15, 1269.
28. V. Dourtoglou, B. Gross, Synthesis 1984, 572.
29. R. T. Pon, S. Yu, Z. Guo, Y. S. Sanghvi, Nucleic Acids Res. 1999, 27, 1531.
30. R. T. Pon, S. Yu, Y. S. Sanghvi, J. Org. Chem. 2002, 67, 856.
31. J. Hartung, S. Hünig, R. Kneuer, M. Schwarz, H. Wenner, Synthesis 1997, 1433.
32. R. K. Kumar, D. R. Davis, J. Org. Chem. 1995, 60, 7726.
33. H. Vu, B. L. Hirschbein, Tetrahedron Lett. 1991, 32, 3005.
34. R. P. Iyer, L. R. Phillips, W. Egan, J. B. Regan, S. L. Beaucage, J. Org. Chem. 1990, 55, 4693.
35. B. Bogumil, G. Tadeusz, G. Eugeniusz, M. Zbigniew, S. Lucjan, J. Chem. Soc. Perkin Trans. 2 1991, 1643.
36. A. P. Guzaev, M. Manoharan, J. Org. Chem. 2001, 66, 1798.
37. H. M. Hsiung, Tetrahedron Lett. 1982, 52, 5119.
38. M. Sekine, A. Ohkubo, K. Seio, J. Org. Chem. 2003, 68, 5478.
39. C. McCollum, A. Andrus, Tetrahedron Lett. 1991, 32, 4069.
40. B. Sproat, F. Colonna, B. Mullah, D. Tsou, A. Andrus, A. Hampel, R. Vinayak, Nucleosides Nucleotides 1995, 14, 255.
41. K. N. G. Chiong, S. D. Lewis, J. A. Shafer, J. Am. Chem. Soc. 1975, 97, 418.