Synthesis of Entecavir (BMS-200475)

Tetrahedron Letters

Volumn 53, Issue 5, 2012, Pages 502-504

  Zhou, Bing ^a   Li, Yuanchao ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

BMS 200475; Entecavir; Hepatitis B virus; Highly diastereoselective; Intramolecular nitrile oxide cycloaddition

Indexed keywords

ENTECAVIR;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG FORMULATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HEPATITIS B VIRUS; INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION; STEREOCHEMISTRY; SWERN OXIDATION;

HEPATITIS B VIRUS;

EID: 84355162293     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.11.073     Document Type: Article

References (20)

1. A. Regev, and E.R. Schiff Adv. Inter. Med. 46 2001 107
2. S.F. Innaimo, M. Sieffer, G.S. Bisacchi, N. Standring, R. Zahler, and R.J. Colonno Antimicrob. Agents Chemother. 41 1997 1444
3. R.A. De Man, L.M.M. Wolters, F. Nevens, D. Chua, M. Sherman, C.L. Lai, A. Gadano, Y. Lee, F. Mazzotta, N. Thomas, and D. DeHertogh Hepatology 34 2001 578
4. C. Lai, M. Rosmawati, J. Lao, H. Vlierberghe, F. Anderson, N. Thomas, and D.J. De Hertogh Hepatology 34 2001 24
5. G.S. Bisacchi, S.T. Chao, C. Bachand, J.P. Daris, S.F. Innaimo, G.A. Jacobs, O. Kocy, P. Lapointe, A. Martel, Z. Merchant, W.A. Slusarchyk, J.E. Sundeen, M.G. Young, R.J. Colonno, and R. Zahler Bioorg. Med. Chem. Lett. 7 1997 127
6. G.S. Bisacchi, S.T. Chao, C. Bachard, J.P. Daris, S. Innaimo, G.A. Jacobs, O. Kocy, P. Lapointe, A. Martel, Z. Merchant, W.A. Slusarchyk, J.E. Sundeen, M.G. Young, R. Colonno, and R. Zahler Bioorg. Med. Chem. Lett. 7 1997 127
7. Bisacchi, G. S.; Sundeen, J. E. W.O. Patent 9809964, 1998.
8. Pendri, Y. R.; Chen, C. P. H.; Patel, S. S. et al. U.S. Patent 0192912, 2004.
9. L.W. Guo, Y.J. Xiao, and L.P. Yang Chin. Chem. Lett. 17 2006 907
10. F.E. Ziegler, and M.A. Sarpong Tetrahedron 59 2003 9013
11. Zhou, M. X.; Reiff, E. A. et al. U.S. Patent 7786300, 2010.
12. For reviews on the Swern oxidation, see: T.T. Tidwell Synthesis 1990 857
13. T.T. Tidwell Org. React. 39 1990 297
14. R.E. Ireland, and D.W. Norbeck J. Org. Chem. 50 1985 2198
15. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765
16. R.A. Johnson, and K.B. Sharpless I. Ojima, Catalytic Asymmetric Synthesis 1993 VCH New York 103 105
17. S. Okamoto, Y. Kobayashi, H. Kato, K. Hori, T. Takahashi, J. Tsuji, and F. Sato J. Org. Chem. 53 1988 5590
18. T.K.M. Shing, W.F. Wong, H.M. Cheng, W.S. Kwok, and K.H. So Org. Lett. 9 2007 753
19. D.P. Curran J. Am. Chem. Soc. 104 1982 4024
20. C. Bonnal, C. Chavis, and M. Lucas J. Chem. Soc. Perkin Trans. 1 1994 1401