1,3-Dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3, 2-diazaphospholidinium hexafluorophosphate (MNTP): A powerful condensing reagent for phosphate and phosphonate esters

Tetrahedron

Volumn 62, Issue 15, 2006, Pages 3667-3673

  Oka, Natsuhisa ^a   Shimizu, Mamoru ^a   Saigo, Kazuhiko ^a   Wada, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Alkylphosphonate; Boranophosphate; H Phosphonate; Phosphate; Phosphonium type condensing reagent

Indexed keywords

1,3 DIMETHYL 2 (3 NITRO 1,2,4 TRIAZOL 1 YL) 2 PYRROLIDIN 1 YL 1,3,2 DIAZAPHOSPHOLIDINIUM HEXAFLUOROPHOSPHATE; ALCOHOL; PHOSPHATE; PHOSPHONIC ACID ESTER; PHOSPHONIUM DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL REACTION; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; THEORETICAL STUDY;

EID: 33645014392     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.084     Document Type: Article

References (38)

1. M.H. Caruthers Chimia 59 2005 38 42
2. Y. Hayakawa Bull. Chem. Soc. Jpn. 74 2001 1547 1565
3. B.V.L. Potter, and D. Lampe Angew. Chem., Int. Ed. Engl. 34 1995 1933 1972
4. Y. Watanabe Selective Reactions and Total Synthesis of Inositol Phosphates A. Rahman Stereoselective Synthesis. Part K Studies in Natural Products Chemistry Vol. 18 1996 Elsevier Amsterdam 391 456
5. E.E. Nifantiev, M.K. Grachev, and S.Y. Burmistrov Chem. Rev. 100 2000 3755 3799
6. S.L. Beaucage, and R.P. Iyer Tetrahedron 49 1993 10441 10448
7. J.S. McMurray, D.R. Coleman IV, W. Wang, and M.L. Campbell Biopolymers 60 2001 3 31
8. S.L. Beaucage, and M.H. Caruthers Tetrahedron Lett. 22 1981 1859 1862
9. S.L. Beaucage, and R.P. Iyer Tetrahedron 48 1992 2223 2311
10. E. Nurminen, and H. Lönnberg J. Phys. Org. Chem. 17 2004 1 17
11. J. Michalski, and W. Dabkowski Top. Curr. Chem. 232 2004 93 144
12. Y. Hayakawa, M. Hirose, M. Hayakawa, and R. Noyori J. Org. Chem. 60 1995 925 930
13. B.C. Froehler, P.G. Ng, and M.D. Matteucci Nucleic Acids Res. 14 1986 5339 5407
14. J. Zhang, T. Terhorst, and M.D. Matteucci Tetrahedron Lett. 38 1997 4957 4960
15. A.P. Higson, A. Sierzchala, H. Brummel, Z. Zhao, and M.H. Caruthers Tetrahedron Lett. 39 1998 3899 3902
16. Z.A. Sergueeva, D.S. Sergueev, and B.R. Shaw Nucleosides Nucleotides 19 2000 275 282
17. T. Wada, Y. Sato, F. Honda, S. Kawahara, and M. Sekine J. Am. Chem. Soc. 119 1997 12710 12721
18. T. Wada, M. Shimizu, N. Oka, and K. Saigo Tetrahedron Lett. 43 2002 4137 4140
19. M. Shimizu, T. Wada, N. Oka, and K. Saigo J. Org. Chem. 69 2004 5261 5268
20. B. Castro, and J.R. Dormoy Tetrahedron Lett. 13 1972 4747 4750
21. J. Coste, D. Le-Nguyen, and B. Castro Tetrahedron Lett. 31 1990 205 208
22. J. Coste, E. Frerot, and P. Jouin J. Org. Chem. 59 1994 2437 2446
23. S.-Y. Han, and Y.-A. Kim Tetrahedron 60 2004 2447 2467
24. J. Kehler, A. Püschl, and O. Dahl Tetrahedron Lett. 37 1996 8041 8044
25. J.-M. Campagne, J. Coste, and P. Jouin J. Org. Chem. 60 1995 5214 5223
26. S.A.N. Hashimi, M. Adiraj, A. Kumar, and S.B. Katti Nucleosides Nucleotides 13 1994 1059 1067
27. D. Molko, A. Guy, and R. Teoule Nucleosides Nucleotides 1 1982 65 80
28. J.E. Marugg, P. Piel, L.W. McLaughlin, M. Tromp, G.H. Veeneman, G.A. van der Marel, and J.H. van Boom Nucleic Acids Res. 12 1984 8639 8651
29. C.B. Reese, R.C. Tatmas, and L. Yau Tetrahedron Lett. 19 1978 2727 2730
30. We synthesized 8 in a different way from the original one in the literature. F. Ramirez, A.V. Patwardham, H.J. Kugler, and C.P. Smith J. Am. Chem. Soc. 89 1967 6276 6282 For the experimental details, see the Supplementary data
31. E.A. Dennis, and F.H. Westheimer J. Am. Chem. Soc. 88 1966 3431 3432
32. 3. Z.M. Jaszay, I. Petnehazy, and L. Toke Heteroat. Chem. 15 2004 447 450
33. We consider the pathway in which 12a is generated directly from 14a can be excluded because it is known that the direct nucleophilic attack of a hydroxyl group to this type of pyrophosphate is extremely slow without the assistance of strong bases or nucleophilic catalysts. S. Chandrasegaran, A. Murakami, and L. Kan J. Org. Chem. 49 1984 4951 4957
34. See the Supplementary data.
35. Compound 2 did not react with alcohols even in the presence of N,N,N′,N′-tetramethyl-1,8-naphthalenediamine.
36. Frisch, M, J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.03, Gaussian, Inc.: Pittsburgh PA, 2003.
37. Kong, J.; White, C. A.; Krylov, A. I.; Sherrill, C. D.; Adamson, R. D.; Furlani, T. R.; Lee, M. S.; Lee, A. M.; Gwaltney, S. R.; Adams, T. R.; Ochsenfeld, C.; Gilbert, A. T. B.; Kedziora, G. S.; Rassolov, V. A.; Maurice, D. R.; Nair, N.; Shao, Y.; Besley, N. A.; Maslen, P. E.; Dombroski, J. E.; Dachsel, H.; Zhang, W. M.; Korambath, P. P.; Baker, J.; Byrd, E. F. C.; Van Voorhis, T.; Oumi, M.; Hirata, S.; Hsu, C. P.; Ishikawa, N.; Florian, J.; Warshel, A.; Johnson, B. G.; Gill, P. M. W.; Head-Gordon, M.; Pople, J. A. Spartan'04, Wavefunction, Inc.: Irvine, CA, 2004.
38. V.B. Oza, and R.C. Corcoran J. Org. Chem. 60 1995 3680 3684