A new efficient and practical synthesis of 2-deoxy-L-ribose

Tetrahedron

Volumn 61, Issue 18, 2005, Pages 4341-4346

  Cho, Bong Hwan ^a   Kim, Jin Hwan ^a,b   Jeon, Heung Bae ^a   Kim, Kwan Soo ^a  

^a Yonsei University   (South Korea)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

Epoxide ring opening; L Enantiomer; Large scale synthesis; Nitrile

Indexed keywords

2 DEOXY LEVO RIBOSE; 3,4 EPOXY 1,2 O ISOPROPYLIDENEBUTANE 1,2 DIOL; ASCORBIC ACID; BUTANEDIOL; RIBOSE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHROMATOGRAPHY; DRUG SYNTHESIS; PRIORITY JOURNAL; PURIFICATION;

EID: 17044420476     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.001     Document Type: Article

References (51)

1. M. Okabe, R.-C. Sun, S.Y.-K. Tam, L.J. Todaro, and D.L. Coffen J. Org. Chem. 53 1988 4780 4786
2. R.F. Schinazi, G. Gosselin, A. Faraj, B.E. Korba, D.C. Liotta, C.K. Chu, C. Mathe, J.-L. Imbach, and J.-P. Sommadossi Antimicrob. Agents Chemother. 38 1994 2172 2174
3. G. Gosselin, C. Mathe, M.-C. Bergogne, A.-M. Aubertin, A. Kirn, R.F. Schinazi, J.-P. Sommadossi, and J.-L. Imbach C. R. Acad. Sci. Paris Sci. Vie 317 1994 85 89
4. L.A. Agrofoglio, and S.R. Challand The chemistry of l-Nucleosides 1998 Kluwer Academic Dordrecht pp 285-319
5. C.K. Chu, T.W. Ma, K. Shanmuganathan, C.G. Wang, Y.J. Xiang, S.B. Pai, G.Q. Yao, J.-P. Sommadossi, and Y.-C. Cheng Antimicrob. Agents Chemother. 39 1995 979 981
6. S. Spadari, G. Maga, F. Focher, G. Ciarrocchi, R. Manservigi, F. Arcamone, M. Capobianco, A. Carcuro, F. Colonna, S. Iotti, and A. Garbesi J. Med. Chem. 35 1992 4214 4220
7. C.-N. Chang, S.-L. Doong, J.H. Zhou, J.W. Beach, L.S. Jeong, C.K. Chu, C.-H. Tsai, and Y.-C. Cheng J. Biol. Chem. 267 1992 13938 13942
8. C.-N. Chang, V. Skalski, J.H. Zhou, and Y.-C. Cheng J. Biol. Chem. 267 1992 22414 22420
9. J.W. Beach, L.S. Jeong, A.J. Alves, D. Pohl, H.O. Kim, C.-N. Chang, S.-L. Doong, R.F. Schinazi, Y.-C. Cheng, and C.K. Chu J. Org. Chem. 57 1992 2217 2219
10. H.O. Kim, S.K. Ahn, A.J. Alves, J.W. Beach, L.S. Jeong, B.G. Choi, P. Van Roey, R.F. Schinazi, and C.K. Chu J. Med. Chem. 35 1992 1987 1995
11. L.K. Hoong, L.E. Strange, D.C. Liotta, G.W. Koszalka, C.L. Burns, and R.F. Schinazi J. Org. Chem. 57 1992 5563 5565
12. R.F. Schinazi, A. McMillan, D. Cannon, R. Mathis, R.M. Lloyd, A. Peck, J.-P. Sommadossi, M. St. Clair, J. Wilson, P.A. Furman, G. Painter, W.B. Choi, and D.C. Liotta Antimicrob. Agents Chemother. 36 1992 2423 2431
13. P.A. Furman, M. Davis, D.C. Liotta, M. Paff, L.W. Frick, D.J. Nelson, R.E. Dornsife, J.A. Wurster, L.J. Wilson, J.A. Fyfe, J.V. Tuttle, W.H. Miller, L. Condreay, D.R. Averett, R.F. Schinazi, and G.R. Painter Antimicrob. Agents Chemother. 36 1992 2686 2692
14. M.M. Mansuri, V. Farina, J.E. Starrett Jr, D.A. Benigni, V. Brankovan, and J.C. Martin Bioorg. Med. Chem. Lett. 1 1991 65 68
15. T.S. Lin, M.Z. Luo, M.C. Liu, S.B. Pai, G.E. Dutschman, and Y.-C. Cheng J. Med. Chem. 37 1994 798 803
16. G. Gosselin, R.F. Schinazi, J.-P. Sommadossi, C. Mathe, M.-C. Bergogne, A.-M. Aubertin, A. Kirn, and J.-L. Imbach Antimicrob. Agents Chemother. 38 1994 1292 1297
17. P.J. Bolon, P.Y. Wang, C.K. Chu, G. Gosselin, V. Boudou, C. Pierra, C. Mathe, J.-L. Imbach, A. Faraj, M.A. Alaoui, J.-P. Sommadossi, S.B. Pai, Y.-L. Zhu, J.-S. Lin, Y.-C. Cheng, and R.F. Schinazi Bioorg. Med. Chem. Lett. 6 1996 1657 1662
18. S. Fujimori, K. Shudo, and Y. Hashimoto J. Am. Chem. Soc. 112 1990 7436 7438
19. M.J. Damha, P.A. Giannaris, P. Marfey, and L.S. Reid Tetrahedron Lett. 32 1991 2573 2576
20. U. Asseline, J.-F. Hau, S. Czernecki, T.L. Diguarher, M.-C. Perlat, J.-M. Valery, and N.T. Thuong Nucleic Acids Res. 19 1991 4067 4074
21. J. Goodchild Bioconjugate Chem. 1 1990 165 187
22. E. Uhlmann, and A. Peyman Chem. Rev. 90 1990 543 584
23. S.L. Beaucage, and R.P. Iyer Tetrahedron 49 1993 6123 6194
24. Y. Hashimoto, N. Iwanami, S. Fujimori, and K. Shudo J. Am. Chem. Soc. 115 1993 9883 9887
25. M.J. Damha, P.A. Giannaris, and P. Marfey Biochemistry 33 1994 7877 7885
26. H. Uchimiya, T. Furukawa, M. Okamoto, Y. Nakajima, S. Matsushita, R. Ikeda, T. Gotanda, M. Haraguchi, T. Sumizawa, M. Ono, M. Kuwano, T. Kanzaki, and S. Akiyama Cancer Res. 62 2002 2834 2839
27. R. Ikeda, T. Furukawa, M. Kitazono, K. Ishitsuka, H. Okumura, A. Tani, T. Sumizawa, M. Haraguchi, M. Konatsu, H. Uchimiya, X.Q. Ren, T. Motoya, K. Yamada, and S. Akiyama Biochem. Biophys. Res. Commun. 291 2002 806 812
28. Y. Nakajima, T. Gotanda, H. Uchimiya, T. Furukawa, M. Haraguchi, R. Ikeda, T. Sumizawa, H. Yoshida, and S. Akiyama Cancer Res. 64 2004 1794 1801
29. R.E. Deriaz, W.G. Overend, M. Stacey, E.G. Teece, and L.F. Wiggins J. Chem. Soc. 1949 1879 1883
30. M.E. Jung, and Y. Xu Org. Lett. 1 1999 1517 1519
31. W.J. Zhang, K.S. Ramasamy, and D.R. Averett Nucleosides Nucleotides 18 1999 2357 2365
32. Z.-D. Shi, B.-H. Yang, and Y.-L. Wu Tetrahedron 58 2002 3287 3296
33. Y. Chong, and C.K. Chu Carbohydr. Res. 337 2002 397 402
34. A.J. Stewart, R.M. Evans, A.C. Weymouth-Wilson, A.R. Cowley, D.J. Watkin, and G.W.J. Fleet Tetrahedron: Asymmetry 13 2002 2667 2672
35. K.S. Kim, Y.H. Ahn, E.Y. Hurh, and E.J. Lee J. Korean Chem. Soc. 34 1994 783 784
36. F. Fazio, and M.P. Schneider Tetrahedron: Asymmetry 11 2000 1869 1876
37. F. Fazio, and M.P. Schneider Tetrahedron: Asymmetry 12 2001 2143 2145
38. K.G.A. Jackson, and J.K.N. Jones Can. J. Chem. 47 1969 2498 2501
39. C.C. Wei, S. De Bernardo, J.P. Tengi, J. Borgese, and M. Weigele J. Org. Chem. 50 1985 3462 3467
40. E. Abushanab, P. Vemishetti, R.W. Leiby, H.K. Singh, A.B. Mikkilineni, D.C.-J. Wu, R. Saibaba, and R.P. Panzica J. Org. Chem. 53 1988 2598 2602
41. K.S. Kim, I.H. Cho, Y.H. Ahn, and J.I. Park J. Chem. Soc., Perkin Trans. 1 1995 1783 1786
42. A. Sivaramakrishnan, G.T. Nadolski, I.A. McAlexander, and B.S. Davidson Tetrahedron Lett. 43 2002 213 216
43. Y. Le Merrer, C. Gravier-Pelletier, J. Dumas, and J.C. Depezay Tetrahedron Lett. 31 1990 1003 1006
44. M. Pottie, J. Van der Eycken, and M. Vandewalle Tetrahedron: Asymmetry 2 1991 329 330
45. C. Vargeese, and E. Abushanab J. Org. Chem. 55 1990 4400 4403
46. D. Mitchell, and T.M. Koenig Tetrahedron Lett. 33 1992 3281 3284
47. S.Y. Ko, H. Masamune, and K.B. Sharpless J. Org. Chem. 52 1987 667 671
48. J.W. Zubrick, B.I. Dunbar, and H.D. Durst Tetrahedron Lett. 16 1975 71 74
49. E.J. Corey, J.W. Ponder, and P. Ulrich Tetrahedron Lett. 21 1980 137 140
50. Y. Kita, O. Tamura, F. Itoh, H. Yasuda, H. Kishino, Y.Y. Ke, and Y. Tamura J. Org. Chem. 53 1988 554 561
51. G. Nakaminami, S. Shioi, Y. Sugiyama, S. Isemura, M. Shibuya, and M. Nakagawa Bull. Chem. Soc. Jpn. 45 1972 2624 2634