Practical synthesis of 1′-substituted Tubercidin C-nucleoside analogs

Tetrahedron Letters

Volumn 53, Issue 5, 2012, Pages 484-486

  Metobo, Sammy E ^a   Xu, Jie ^a   Saunders, Oliver L ^a   Butler, Thomas ^a   Aktoudianakis, Evangelos ^a   Cho, Aesop ^a   Kim, Choung U ^a  

^a GILEAD SCIENCES   (United States)

Author keywords

C nucleosides; Chelation; Stereoselective; Tubercidin

Indexed keywords

NUCLEOPHILE; NUCLEOSIDE DERIVATIVE; RIBOSE; TUBERCIDIN C NUCLEOSIDE DERIVATIVE; TUBERCIDIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; LITHIATION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 84355162282     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.11.055     Document Type: Article

References (22)

1. Q. Wu, and C. Simons Synthesis 10 2004 1533
2. J. Stambasky, M. Hocek, and P. Kocovsky Chem. Rev. 109 2009 6729
3. D.E. Bergstrom, A.J. Brattesani, M.K. Ogawa, P.A. Reddy, M.J. Schweickert, J. Balzarini, and E. De Clerq J. Med. Chem. 27 3 1984 285
4. S.A. Patil, B.A. Otter, and R.S. Klein Tetrahedron Lett. 35 1994 5339
5. M.F.A. Adamo, R.M. Adlington, J.E. Baldwin, and A.L. Day Tetrahedron 60 2004 841
6. R.A. Adlington, J.E. Baldwin, G.J. Pritchard, and K.C. Spencer Tetrahedron Lett. 41 2000 575
7. Biocryst Pharmaceuticals WO 2008/089105 A2.
8. G. Butora, D.B. Olsen, S.S. Carroll, D.R. McMassters, C. Schmitt, J.F. Leone, M. Stahlhut, C. Burlein, and M. MacCoss Bioorg. Med. Chem. 15 2007 5219
9. K.S. Gudmundsson, J.C. Drach, and L.B. Townsend J. Org. Chem. 63 1998 984
10. E. Clazada, C.A. Clarke, C. Roussin-Bouchard, and R.H. Wightman J. Chem., Soc., Perkin Trans. 1 1995 517
11. J.A. Piccirilli, T. Krauch, L.J. Macpherson, and S.A. Benner Helv. Chim. Acta 1991 397
12. Bayer US patent WO2006-US46081.
13. L. Alessandrini, S. Casati, P. Ciuffreda, R. Ottria, and E. Santaniello J. Carb. Chem. 27 2008 332
14. S. Djuric, J. Venit, and P. Magnus Tetrahedron Lett. 22 1981 1787
15. S. Hildbrand, A. Blaser, S.P. Parel, and C.J. Leumann J. Am. Chem. Soc. 119 1997 5499 5511
16. J. Matulic-Adamic, and L. Beigelman Tetrahedron Lett. 38 1997 1669 1672
17. S.R. Shenoy, D.M. Smith, and K.A. Woerpel J. Am. Chem. Soc. 128 26 2006 8671
18. H.-U. Reissig, and A. Schmitt Synlett 1990 40
19. M. Prevost, O. St-Jean, and Y. Guindon J. Am. Chem. Soc. 132 2010 12433
20. C.H. Larsen, B.H. Ridgeway, J.T. Shaw, and K.A. Worpel J. Am. Chem. Soc. 121 1999 12208
21. J.T. Shaw, and K.A. Woerpel Tetrahedron 55 1999 8747
22. C.H. Larsen, B.H. Ridgway, J.T. Shaw, D.M. Smith, and K.A. Woerpel J. Am. Chem. Soc. 2005 10879