51. Synthesis of 1,6-dideoxynojirimycin, 1,6-dideoxy-D-allo-nojirimycin, and 1,6-dideoxy-D-gulo-nojirimycin via asymmetric hetero-Diels-Alder reactions

Helvetica Chimica Acta

Volumn 79, Issue 2, 1996, Pages 560-567

  Defoin, Albert ^a   Sarazin, Hervé ^a   Streith, Jacques ^a  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 DIDEOXYNOJIRIMYCIN; CARBOHYDRATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029935459     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19960790223     Document Type: Article

References (26)

1. Ch.-H. Wong, T. Kajimoto, K. K.-C. Liu, L. Chen, PCT Int. Appl. WO. 92 21657 (CA . 1993, 118, 192187); Ch.-H. Wong, Y. Ichikawa, G. J. Shen, PCT Int. Appl. WO. 92 16640 (CA : 1993, 118, 186950).
2. Ch.-H. Wong, T. Kajimoto, K. K.-C. Liu, L. Chen, PCT Int. Appl. WO. 92 21657 (CA . 1993, 118, 192187); Ch.-H. Wong, Y. Ichikawa, G. J. Shen, PCT Int. Appl. WO. 92 16640 (CA : 1993, 118, 186950).
3. D. P. Dumas, T. Kajimoto, K. K.-C. Liu, Ch.-H. Wong, D. B. Berkowitz, S. J. Danishefsky, Bioorg. Med. Chem. Lett 1992, 2, 33.
4. G. W. J. Fleet, A. N. Shaw, St. V. Evans, L. E. Fellows, J Chem. Soc., Chem. Commun. 1985, 841.
5. S. Washiyama, A. Kamiya, S Esaki, A Tanaka, N. Sugiyama, Sh. Kamiya, Biosci. Biotechnol. Biochem. 1993, 57, 847.
6. P. Zhou, H. M. Salleh, Ph. C. M. Chan, G. Lajoie, J. F. Honek, P. T. Ch. Nambiar, O. P. Ward, Carbohydr. Res. 1993, 259, 155.
7. H. Paulsen, M. Matzke, Liebigs Ann. Chem. 1988, 1121.
8. G. W. J. Fleet, S. Petursson, A. L. Campbell, R. A Mueller, J R. Behling, K. A. Babiak, J. S. Ng, M. G. Scaros, J. Chem. Soc., Perkin Trans. 1 1989, 665; Sh. Takahashi, H Kuzuhara, Chem. Lett. 1992, 21.
9. G. W. J. Fleet, S. Petursson, A. L. Campbell, R. A Mueller, J R. Behling, K. A. Babiak, J. S. Ng, M. G. Scaros, J. Chem. Soc., Perkin Trans. 1 1989, 665; Sh. Takahashi, H Kuzuhara, Chem. Lett. 1992, 21.
10. a) T. Kajimoto, L. Chen, K K.-C. Liu, Ch.-H. Wong, J. Am. Chem. Soc. 1991, 113, 6678;
11. b) K. K.-C. Liu, T. Kajimoto, L. Chen, Z. Zhong, Y. Ichikawa, Ch.-H. Wong, J. Org. Chem 1991, 56, 6280;
12. 1H-NMR data for 1,6-dideoxynojirimycin).
13. A. Defoin, H. Sarazin, J. Streith, Tetrahedron Lett. 1993, 34, 4327.
14. A. Defoin, H. Fritz, G. Geffroy, J. Streith, Helv. Chim. Acta 1988, 71, 1642.
15. a) H. Felber, G. Kresze, R. Prewo, A. Vasella, Helv. Chim. Acta 1986, 69, 1137; corrigendum: H. Braun, R. Charles, G. Kresze, M. Sabuni, J. Winkler, Liebigs Ann. Chem. 1987, 1129;
16. b) H. Braun, H. Felber, G. Kresze, Fr. P. Schmidtchen, R. Prewo, A. Vasella, ibid. 1993, 261.
17. A. Defoin, H. Sarazin, J. Streith, Synlett. 1995, 34, 1187.
18. A. Hussain, P. B. Wyatt, Tetrahedron 1993, 49, 2123.
19. A. Defoin, H. Sarazin, Ch. Strehler, J. Streith, Tetrahedron Lett. 1994, 35, 5653.
20. R. Kuhn, M. Hoffer, Chem. Ber. 1931, 64, 1977
21. V. Van Rheenen, R. C. Kelly, D. Y. Cha, Tetrahedron Lett. 1976, 17, 1973
22. a) Y. Gao, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 7538;
23. b) B. M. Kim, K. B. Sharpless, Tetrahedron Lett. 1989, 30, 655.
24. H. Paulsen, Kl. Todt, H. Ripperger, Chem. Ber. 1968, 101, 3365
25. K. Akashi, R. E. Palermo, K. B. Sharpless, J. Org. Chem 1978, 43, 2063.
26. A Defoin, J. Pires, J. Streith, Helv Chim. Acta 1991, 74, 1653.