O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU): A new reagent for the cleavage of tetrahydropyranyl, silyl and 4,4'- dimethoxytrityl ethers

Synlett

Volumn , Issue 6, 1999, Pages 709-712

  Ramasamy, Kanda S ^a   Averett, Devron ^a  

^a Valeant Pharmaceuticals International   (United States)

Author keywords

Cleavage; DMT; TBTU; THP

Indexed keywords

NUCLEOSIDE; O (BENZOTRIAZOL) N,N,N',N' TETRANETHYLURONUIM TETRAFLUOBORATE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033067725     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2724     Document Type: Article

References (31)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991.
2. Bernady, K. F.; Floyd, M. B.; Poletto, J. F.; Weiss, M. J. J. Org. Chem. 1979, 44, 1438.
3. Johnson, R. D.; Marston, C. R.; Krieger, P. E.; Goe, G. L. Synthesis 1988, 393.
4. Otera, J.; Nozaki, H. Tetrahedron Lett. 1986, 27, 5743.
5. Wagner, A.; Heitz, M.-P.; Mioskowski, C. J. Chem. Soc., Chem. Commun. 1989, 1619.
6. Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
7. Gigg, J.; Gigg, R. J. Chem. Soc. C, 1967, 431.
8. Corey, E. J.; Niwa, H.; Knolle, J. J. Am. Chem. Soc. 1978, 100, 1942.
9. Morizawa, Y.; Mori, I.; Hiyama, T.; Nozaki, H. Synthesis 1981, 899.
10. DattaGupta, A.; Singh, R.; Singh, V. K. Synlett 1996, 69.
11. Raina, S.; Singh, V. K. Synth. Commun. 1995, 25, 2395.
12. Kim, S.; Park, J. H. Tetrahedron Lett. 1987, 28, 439.
13. Ogawa, Y.; Shibasaki, M, Tetrahedron Lett. 1984, 25, 663.
14. Wetter, H.; Oertle, K. Tetrahedron Lett. 1985, 26, 5515.
15. Metcalf, B. W.; Burkhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35.
16. Corey, E. J.; Yi, K. Y. Tetrahedron Lett. 1992, 33, 2289.
17. Pilcher, A. S.; Hill, D. K.; Shimsock, S. J.; Waltermire, R. E.; DeShong, P. J. Org. Chem. 1992, 57, 2492.
18. Dahlhoff, W. V.; Taba, K. M. Synthesis 1986, 561.
19. Tanemura, K.; Suzuki, T.; Horaguchi, T. J. Chem. Perkin Trans. 1, 1992, 2997.
20. Corey, E. J.; Jones, G. B. J. Org. Chem. 1992, 57, 1028.
21. Newton, R. F.; Reynolds, D. P. Tetrahedron Lett. 1979, 20, 3981.
22. Cormier, J. F. Tetrahedron Lett, 1991, 32, 187.
23. Prakash, C.; Saleh, S.; Blair, I. A. Tetrahedron Lett. 1989, 30, 19.
24. Wilson, N. S.; Keay, B. A. Tetrahedron Lett. 1996, 37, 153; Wilson, N. S.; Keay, B. A. J. Org. Chem. 1996, 61, 2918.
25. Wilson, N. S.; Keay, B. A. Tetrahedron Lett. 1996, 37, 153; Wilson, N. S.; Keay, B. A. J. Org. Chem. 1996, 61, 2918.
26. Hosaka, H.; Suzuki, Y.; Sato, H.; Gug-Kim, S.; Takaku, H. Nucleic Adds Res. 1991, 19, 2935.
27. Caruthcrs, M. H. J. Chem. Ed. 1989, 66, 577 and references cited therein.
28. Ravikumar, V. T.; Krotz, A. H.; Cole, D. L. Tetrahedron Lett. 1995, 36, 6587.
29. Leonard, N. J.; Neelima, Tetrahedron Lett. 1995, 36, 7833.
30. Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1929-1930.
31. Lipshutz, B. H.; Harvey, D. F. Synth. Commun. 1982, 12, 267-277.