A convenient method for C-azanucleosides synthesis

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 6079-6082

  Yokoyama, Masataka ^a   Akiba, Takahiro ^a   Ochiai, Yoshie ^a   Momotake, Atsuya ^a   Togo, Hideo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

C NUCLEOSIDE; NUCLEOSIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029801709     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960523i     Document Type: Article

References (30)

1. (a) Togo, H.; Aoki, M.; Yokoyama, M. Tetrahedron Lett. 1991, 32, 6559.
2. (b) Togo, H.; Ishigami, S.; Yokoyama, M. Chem. Lett. 1992, 1673.
3. (c) Togo, H.; Aoki, M.; Kuramochi, T.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1993, 2417.
4. (d) Yokoyama, M.; Tanabe, T.; Toyoshima, A.; Togo, H. Synthesis 1993, 517.
5. (e) Yokoyama, M.; Toyoshima, A.; Akiba, T.; Togo, H. Chem. Lett. 1994, 265.
6. (f) Ishigami, S.; Togo, H.; Yokoyama, M. J. Chem. Soc., Perkin Trans, 1 1994, 2407.
7. (g) Togo, H.; Ishigami, S.; Fujii, M.; Ikuma, T.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1994, 2931.
8. (h) Yokoyama, M.; Akiba, T.; Togo, H. Synthesis 1995, 638.
9. (i) Yokoyama, M.; Nomura, M.; Tanabe, T.; Togo, H. Heteroatom Chem. 1995, 6, 189.
10. (a) Hashimoto, H.; Hayakawa, M. Chem. Lett. 1989, 1881.
11. (b) Legler, G. Adv. Chem. Biochem. 1990, 48, 318.
12. (c) Poitout, L.; Merrer, Y. L.; Depezay, J.-C. Tetrahedron lett. 1994, 35, 3293.
13. (d) Fowler, P. A.; Haines, A. H.; Taylor, R. J. K.; Chrystal, E. J. T.; Gravestock, M. B. J. Chem. Soc., Perkin Trans. 1 1994, 2229.
14. (e) Martin, O. R.; Saavedra, O. M. Tetrahedron Lett. 1995, 36, 799.
15. (f) Ichikawa, M.; Igarashi, Y.; Ichikawa, Y. Tetrahedron Lett. 1995, 36, 1767.
16. (g) Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
17. (h) Hiranuma, S.; Shimizu, T.; Nakata, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 8247. General synthetic method consists of (1) aldolase reaction to the azido keto sugar and (2) Pd/C-mediated reductive amination: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182 and references cited.
18. (h) Hiranuma, S.; Shimizu, T.; Nakata, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 8247. General synthetic method consists of (1) aldolase reaction to the azido keto sugar and (2) Pd/C-mediated reductive amination: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182 and references cited.
19. (a) Just, G.; Donnini, P. Can. J. Chem. 1977, 55, 2998.
20. (b) Horenstein, B. A.; Zabinski, R. F.; Schramm, V. L. Tetrahedron Lett. 1993, 34, 7213.
21. (a) Burckhalter, J. H.; Short, J. H. J. Org. Chem. 1958, 23, 1281.
22. (b) McGhie, J. F.; Ross, W. A.; Laney, D. H. J. Chem. Soc. 1962, 2578.
23. Martin, O. R.; Saavedra, O. M. Tetrahedron Lett. 1995, 36, 799.
24. Kaskar, B.; Heise, G. L.; Michalak, R. S.; Vishnuvajjala, B. R. Synthesis 1990, 1031.
25. Rayner, B.; Tapiero, C.; Inbach, J. L. Carbohydr. Res. 1976, 47, 195.
26. Maeba, I.; Iwata, K.; Usami, F.; Furukawa, H. J. Org. Chem. 1983, 48, 2998.
27. Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777.
28. Bergman, N.-Å.; Halvarsson, T. J. Org. Chem. 1988, 53, 2548.
29. (a) Burckhalter, J. H.; Short, J. H. J. Org. Chem. 1958, 23, 1281.
30. (b) McGhie, J. F.; Ross, W. A.; Laney, D. H. J. Chem. Soc. 1962, 2578.