Synthesis of (+)-nojirimycin from 2,3,4,6-tetra-O-benzyl-D-glucopyranose

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1999, Pages 1403-1406

  Moutcl, Stéphane ^a   Shipman, Michael ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002720469     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. (a) N. Ishida, K. Kumagai, T. Niida, T. Tsuruoka and H. Yumoto, J. Antibiot., Ser. A, 1967, 20, 66;
2. (b) S. Inouye, T. Tsuruoka, T. Ito and T. Niida, Tetrahedron, 1968,24,2125.
3. D. D. Schmidt, W. Frommer, L. Müller and E. Truscheit, Naturwissenschaften, 1979,66, 584.
4. (a) T. Niwa, S. Inouye, T. Tsuruoka, Y. Koaze and T. Niida, Agric. Biol. Chcm., 1970, 34, 966;
5. (b) E. T. Reese, F. W. Parrish and M. Ettinger, Carbohydr. Res., 1971, 18, 381;
6. G. Hanozet, H.-P. Pircher, P. Vanni, B. Oesch and G. Semenza, J. Biol. Chcm., 1981, 256, 3703.
7. H. lida, N. Yamazaki and C. Kibayashi, J. Org. Chem., 1987, 52, 3337.
8. (a) N. Chida, Y. Furuno and S. Ogawa, J. Chem. Soc., Chem. Commun., 1989, 1230;
9. (b) N. Chida, Y. Furuno, H. Ikemoto and S. Ogawa, Carbohydr. Res., 1992, 237, 185.
10. A. Dondoni, P. Merino and D. Perrone, Tetrahedron, 1993,49,2939.
11. (a) H. Saeki and E. Ohki, Chem. Pharm. Bull., 1968, 16, 962;
12. (b) H. Saeki and E. Ohki, Chcm. Pharm. Bull., 1968,16, 2477;
13. A. Kiemer, U. Hofmeister and R. Lemmes, Carbohydr. Res., 1979, 68, 391;
14. A. Vasella and R. Voefiray, Heb. Chim. Ada, 1982, 65, 1134;
15. (e) Y. Tsuda, Y. Okuno and K. Kanemitsu, Ueterocycles, 1988, 27,63;
16. (f) Y. Tsuda, Y. Okuno, M. Iwaki and K. Kanemitsu, Chem. Pharm. Bull, 1989, 37, 2673;
17. (g) P. B. Anzeveno and L. J. Creemer, Teirahedron Lett., 1990, 31, 2085;
18. (h) B. Stasik, D. Beaupère, R. Uzan, G. Demailly and C. Morin, C. R Acad. Sci., Sér. II, 1990, 311, 521;
19. V. Sasinkovâ and M. Koôs, Client. Pap., 1997,51, 147.
20. B. Rajanikanth and R. Seshadri, Tetrahedron Lett., 1989,30, 755.
21. G. W. J. Fleet, N. G. Ramsden, N. M. Carpenter, S. Petursson and R. T. Aplin, Tetrahedron Lett., 1990,31,405.
22. P. A. Gent and R. Gigg, J. Chem. Soc., Perkin Trans, l, 1974, 1446.
23. S. V. Ley, J. Norman, W. P. Griffith and S. P. Marsden, Synthesis, 1994, 639.
24. A. J. Mancuso and D. Swern, Synthesis, 1981, 165.
25. An attempt to separate this amine mixture by conversion to the corresponding benzyl carbamates was unsuccessful.
26. P. S. Liu, J. Org. Chein., 1987, 52, 4717.