Synthesis of 5-(β-D-ribofuranosyl)-pyridin-2-one: A 'deletion-modified' analogue of uridine

Tetrahedron Letters

Volumn 38, Issue 10, 1997, Pages 1669-1672

  Matulic Adamic, Jasenka ^a   Beigelman, Leonid ^a  

^a Sirna Therapeutics Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; URIDINE DERIVATIVE;

ACETYLATION; ARTICLE; CONFORMATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031562431     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00197-4     Document Type: Article

References (24)

1. 1. For a review of the modified nucleosides utilized in hammerhead ribozyme studies see: McKay, D.B. RNA 1996, 2, 395-403.
2. 2. Burgin, A.B, Jr.; Gonzalez, C.; Matulic-Adamic, J.; Karpeisky, A.M.; Usman, N.; McSwiggen, J.A.; Beigelman, L. Biochemistry 1996, 55, 14091-14097.
3. 3. Murray, J.B.; Adams, C.J.; Arnold, J.R.P.; Stockley, P.G. Biochem. J. 1995, 311, 487-494.
4. 4. Tuschl, T.; Ng, M.M.P.; Pieken, W.; Benseler, F.; Eckstein, F. Biochemistry 1993, 32, 11658-11668.
5. 5. Bevers, S.; Xiang, G.; McLaughlin, L.W. Biochemistry 1996, 35, 6483-6490 and references cited therein.
6. 6. Matulic-Adamic, J.; Beigelman, L. Tetrahedron Lett. 1997, in press.
7. 7. Recently, the preparation of 2-amino analog of 2 was reported: Hildbrand, S.; Leumann, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 1968-1970.
8. 8. Starzewski, P.; Tamm, C. Angew. Chem. Int. Ed. Engl. 1990, 29, 36-57.
9. 9. Sieburth, S. McN.; Hiel, G.; Lin, C-H.; Kuan, D.P. J. Org. Chem. 1994, 59, 80-87.
10. 10. Drew, M.G.B.; Mann, J.; Thomas, A. J. Chem. Soc., Perkin Trans. 1 1986, 2279-2285.
11. 11. It should be noted that for hemiacetals 6, 10 and 11, the prefix α refers to the position of the glycosidic OH group relative to the configuration at the reference C-atom (C4′ in 2; i.e. the pyridyl moiety is in the β-position).
12. 12. Tapiero, C.; Imbach, J.-L. In Nucleic Acid Chemistry, Part 1, pp. 1055-1059, Townsend, L.B. and Tipson, R.S., Eds.; J. Wiley & Sons, Inc.: New York, 1978. Ohrui, H.; Jones, G.H.; Moffatt, J.G.; Maddox, M.L.; Christensen, A.T.; Byram, S.K. J. Amer. Chem. Soc. 1975, 97, 4602-4613.
13. 12. Tapiero, C.; Imbach, J.-L. In Nucleic Acid Chemistry, Part 1, pp. 1055-1059, Townsend, L.B. and Tipson, R.S., Eds.; J. Wiley & Sons, Inc.: New York, 1978. Ohrui, H.; Jones, G.H.; Moffatt, J.G.; Maddox, M.L.; Christensen, A.T.; Byram, S.K. J. Amer. Chem. Soc. 1975, 97, 4602-4613.
14. 13. Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412.
15. 14. Gudmundsson, K.S.; Drach, J.D.; Townsend, L.B. Tetrahedron Lett. 1996, 37, 2365-2368.
16. 15. Parham, W.E.; Piccirilli, R.M. J. Org. Chem. 1977, 42, 257-260.
17. 16. Tam, S., Y.-K.; Klein, R.S.; de las Heras, F.G.; Fox, J.J. J. Org. Chem. 1979, 44, 4854-4862.
18. 17. Sokolova, T.N.; Yartseva, I.V.; Preobrazhenskaya, M.N. Carbohydr. Res. 1981, 93, 19-34.
19. 5″,5′=12.4, 1H, H5″).
20. 19. Hsieh, H.-P.; McLaughlin, L.W. J. Org. Chem. 1995, 60, 5356-5359.
21. 20. Timpe, W.; Dax, K.; Wolf, N.; Weidman, H. Carbohydr. Res. 1975, 39, 53-60.
22. 21. Kraus, G.A.; Molina, M.T. J. Org. Chem. 1988, 53, 752-753.
23. 5″,4′=3.6, J5″,5′=10.5, 1H, H5″).
24. 5″,5′=11.9, 1H, H5″).