Selective deprotection of tert-butyldimethylsilyl ether with lithium bromide and 18-crown-6

Synthetic Communications

Volumn 27, Issue 17, 1997, Pages 2953-2959

  Tandon, Manish ^a   Begley, Tadhg P ^a  

^a Department of Molecular Biology and Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CROWN ETHER; DEOXYURIDINE; LITHIUM BROMIDE; TERT BUTYLDIMETHYLSILYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 0030738450     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708005001     Document Type: Article

References (19)

1. (a) Greene, T. W. and Wuts, P. G. M., "Protective groups in Organic Synthesis", John Wiley & Sons, New York 1991.
2. (b) Corey E. J.; Venkatserwarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
3. (a) Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R.; Roberts, S. M. Tetrahedron Lett. 1979, 20, 3981.
4. (b) Liotta, C. L.; Harris, H. P. J. Am. Chem. Soc. 1974, 96, 2250.
5. (c) Nicolaou, K. C.; Webber, S. E. Synthesis 1986, 453.
6. (a) Cunico, R. F.; Bedell, L. J. Org. Chem. 1980, 45, 4797.
7. (b) Prakash, C.; Saleh, S.; Blair, I. A. Tetrahedron Lett. 1989, 30, 19.
8. (a) Kelly, D. R.; Roberts, S. M.; Newton, R. F. Synth. Commun. 1979, 9, 295.
9. (b) Metcalf, B. W.; Burkhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35.
10. (c) Guindon, Y.; Yoakim, C.; Morton, H. E. J. Org. Chem. 1984, 49, 3912.
11. (d) Batten, R. J.; Dixon, A. J.; Taylor, R. J. K.; Newton, R. F. Synthesis 1980, 234.
12. Feixas, J.; Capdevila, A.; Guerrero, A. Tetrahedron 1994, 50, 8539.
13. (a) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117.
14. (b) Kawai, A.; Hara, O.; Hamada, Y.; Shiari, T. Tetrahedron Lett. 1988, 29, 6331.
15. The synthesis of 1 will be reported separately.
16. (a) Ogilvie, K. Can. J. Chem. 1973, 51, 3799.
17. (b) Ogilvie, K.; Thompson, E. A.; Quilliam, M. A.; Westmore, J. B. Tetrahedron Lett. 1974, 2865.
18. The compounds 11 (50%), 10 (30%) and the 2′-deoxyuridine (20%) were obtained.
19. 5Si: 357.1846; found: 357.1846.