Synthesis of 5'-C-branched thymidines and conversion to phosphoramidites

Nucleosides and Nucleotides

Volumn 17, Issue 6, 1998, Pages 1033-1051

  Wang, Guangyi ^a   Middleton, Patrick J ^a  

^a Valeant Pharmaceuticals International   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORAMIDIC ACID DERIVATIVE; THYMIDINE DERIVATIVE;

ARTICLE; NUCLEAR OVERHAUSER EFFECT; NUCLEIC ACID SYNTHESIS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031747733     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319808004219     Document Type: Article

References (19)

1. Crooke, S. T.; Lebleu, B. Antisense Research and Applications; CRC Press: Boca Raton, 1993.
2. Lisziewicz, J.; Sun, D.; Metelev, V.; Zamecnik, P.; Gallo, R. C.; Agrawal, S. Proc. Natl. Acad. Sci. USA 1993, 90, 3860-3864.
3. Stein, C. A.; Cheng, Y. -C. Science 1993, 261, 1004-1012.
4. Uhlmann, E.; Peyman, A. Chemical Reviews 1990, 90, 543-584.
5. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123-94.
6. Sanhvi, Y. S.; Cook, P. D. Carbohydrate Modifications in Antisense Research, ACS Symposium Series, No. 580; American Chemical Society: Washington, D.C., 1994.
7. Inoue, H.; Hayase, Y.; Imura, A.; Iwai, S.; Miuta, K.; Ohtsuka, E. Nucleic Acids Res. 1987, 15, 6131-6147.
8. Lesnik, E. A.; Guinosso, C. J.; Kawasaki, A. M.; Sasmor, H.; Zounes, M.; Cummins, L. L.; Ecker D. J.; Cook, P. D.; Freier, S. M. Biochemistry 1993, 32, 7832-7838.
9. Sproat, B. S.; Lamond, A. I.; Beijer, B.; Neuner, P.; Ryder, U. Nucleic Acids Res. 1989, 17, 3373-3386.
10. Fensholdt, J.; Thrane, H.; Wengel, J. Tetrahedron Lett. 1995, 36, 2535-2538.
11. Maag, H.; Schmidt, B.; Rose S. J. Tetrahedron Lett. 1994, 35, 6449-6452.
12. Wang, G.; Seifert, W. E. Tetrahedron Lett. 1996, 37, 6515-6718.
13. Saha, A. K.; Caulfield, T. J.; Hobbs, C.; Upson, D. A.; Waychunas, C.; Yawman, A. M. J. Org. Chem. 1995, 60, 788-789.
14. Wang, G.; Middleton, P. J. Tetrahedron Lett. 1996, 37, 2739-2742.
15. O-Yang C.; Wu, H. Y.; Fraser-Smith, E. B.; Walker, K. A. M. Tetrahedron Lett. 1992, 33, 37-40.
16. Jones, G. H.; Taniguchi, M.; Tegg, D.; Moffatt, J. G. J. Org. Chem. 1979, 44, 1309-1317.
17. To verify whether the real reagent in this reaction was magnesium bromide, we conducted the reaction of 7 with magnesium bromide in THF and obtained 12 as the only product in high yield. Apparently, it is much more convenient to use magnesium bromide than to use methylmagnesium bromide.
18. Wang, G.; Bergstrom, D. E. Tetrahedron Lett. 1993, 34, 6725-6728.
19. Robins, M. J., Wilson, J. S., Sawyer, L., James, M. N. G. Can. J. Chem. 1983, 61, 1911-1920.