A versatile one-pot procedure to phosphate monoesters and pyrophosphates using Di(p-methoxybenzyl)-N,N-diisopropylphosphoramidite

Organic Letters

Volumn 10, Issue 20, 2008, Pages 4461-4464

  Van Der Heden Van Noort, Gerbrand J ^a   Verhagen, Carlo P ^a   Van Der Horst, Maarten G ^a   Overkleeft, Herman S ^a   Van Der Marel, Gijsbert A ^a   Filippov, Dmitri V ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

DI(P METHOXYBENZYL) N,N DIISOPROPYLPHOSPHORAMIDITE; DI(P-METHOXYBENZYL)-N,N-DIISOPROPYLPHOSPHORAMIDITE; ESTER; ORGANOPHOSPHORUS COMPOUND; PYROPHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

DIPHOSPHATES; ESTERS; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS;

EID: 58149173834     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801608j     Document Type: Article

References (33)

1. McMurray, J. S.; Coleman, D. R.; Wang, W.; Campbell, M. L. Biopolymers 2001, 60, 3-31.
2. Nikolaev, A. V.; Botvinko, I. V.; Ross, A. J. Carbohydr. Res. 2007, 342, 297-344.
3. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 10441-10488.
4. Burgess, K.; Cook, D. Chem. Rev. 2000, 100, 2047-2059.
5. Hindsgaul, O. F.; Fukuda, M. Molecular Glycobiology; Oxford University Press: New York, 1994.
6. Umezawa, S.; Tatsuta, K.; Izawa, O.; Tsuchiya, T. Tetrahedron Lett. 1972, 13, 97-100.
7. Fields, S. C. Tetrahedron 1999, 55, 12237-12272.
8. Kraszewski, A.; Stawinski, J. Pure Appl. Chem. 2007, 79, 2217-2227.
9. Michalski, J.; Dabkowski, W. Top. Curr. Chem. 2004, 232, 93-144.
10. Moriguchi, T.; Asai, N.; Okada, K.; Seio, K.; Sasaki, T.; Sekine, M. J. Org. Chem. 2002, 67, 3290-3300.
11. Burkart, M. D.; Vincent, S. P.; Duffels, A.; Murray, B. W.; Ley, S. V.; Wong, C. H. Bioorg. Med. Chem. 2000, 8, 1937-1946.
12. Klinman, D. M.; Yi, A. K.; Beaucage, S. L.; Conover, J.; Krieg, A. M. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 2879-2883.
13. Stein, C. A.; Subasinghe, C.; Shinozuka, K.; Cohen, J. S. Nucleic Acids Res. 1988, 16, 3209-3221.
14. Bollmark, M.; Stawinski, J. Nucleosides Nucleotides Nucleic Acids 1998, 17, 663-680.
15. Nifantiev, E. E.; Grachev, M. K.; Burmistrov, S. Y. Chem. Rev. 2000, 100, 3755-3799.
16. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123-6194.
17. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311.
18. Ausin, C.; Grajkowski, A.; Cieslak, J.; Beaucage, S. L. Org. Lett. 2005, 7, 4201-4204.
19. Lartia, R.; Asseline, U. Tetrahedron. Lett. 2004, 45, 5949-5952.
20. Nurminen, E.; Lonnberg, H. J. Phys. Org. Chem. 2004, 17, 1-17.
21. Ghisaidoobe, A. B. T.; de Koning, M. C.; Duynstee, H. I.; Ten Kortenaar, P. B. W.; Overkleeft, H. S.; Filippov, D. V.; van der Marel, G. A. Terahedron Lett. 2008, 49, 3129-3132.
22. Kriek, N.; Meeuwenoord, N. J.; van den Eist, H.; Heus, H. A.; van der Marel, G. A.; Filippov, D. V. Org. Biomol. Chem. 2006, 4, 3576-3586.
23. Filippov, D.; Timmers, C. M.; Roerdink, A. R.; van der Marel, G. A.; van Boom, J. H. Terahedron Lett. 1998, 39, 4891-4894.
24. Meyer, A.; Morvan, F.; Vasseur, J. J. Terahedron Lett. 2004, 45, 3745-3748.
25. Dreef, C. E.; Tuinman, R. J.; Lefeber, A. W. M.; Elle, C. J. J.; van der Marel, G. A.; van Boom, J. H. Tetrahedron 1991, 47, 4709-4722.
26. Shuto, S.; Shirato, M.; Sumita, Y.; Ueno, Y.; Matsuda, A. Terahedron Lett. 1998, 39, 7341-7344.
27. Nielsen, J.; Caruthers, M. H. J. Am. Chem. Soc. 1988, 110, 6275-6276.
28. Wittmann, V.; Wong, C. H. J. Org. Chem. 1997, 62, 2144-2147.
29. Cooke, L. A.; Frauendorf, C.; Gilea, M. A.; Holmes, S. C; Vyle, J. S. Terahedron Lett. 2006, 47, 719-722.
30. It became apparent that under the influence of morpholine or isobutylamine the benzoyl protecting group on the nucleobase was removed. This problem was nonexistent when the more stable POM group was used for protection of the thymine base.
31. Chandrasegaran, S.; Murakami, A.; Kan, L. S. J. Org. Chem. 1984, 49, 4951-4957.
32. Ohkubo, A.; Aoki, K.; Seio, K.; Sekine, M. Terahedron Lett. 2004, 45, 979-982.
33. Donahue, M. G.; Johnston, J. N. Bioorg. Med. Chem. Lett. 2006, 16, 5602-5604.