Use of the N-tosyl-activated aziridine 1,2-dideoxy-1,2-iminomannitol as a synthon for 1-deoxymannojirimycin analogues

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2223-2226

  Joly, Gert J ^a   Peeters, Koen ^a   Mao, Hua ^a   Brossette, Thierry ^a   Hoornaert, Georges J ^a   Compernolle, Frans ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Aziridines; Carbohydrates; Mitsunobu reactions; Piperidines

Indexed keywords

1 DEOXYMANNONOJIRIMYCIN; ANTIVIRUS AGENT; AZIRIDINE DERIVATIVE; CARBOHYDRATE; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034719899     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00130-1     Document Type: Article

References (30)

1. (a) Legler, G.; Julich, E. Carbohydr. Res. 1984, 128, 61;
2. (b) Saul, R.; Molyneux, R. J.; Elbein, A. D. Arch. Biochim. Biophys. 1984, 230, 668.
3. Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; de Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature 1987, 330, 74.
4. For a review, see: Olden, K.; Breton, P.; Grzegorzewski, K.; Yasuda, Y.; Gause, B. L.; Oredipe, O. A.; Newton, S. A.; White, S. L. Pharmacol. Ther. 1991, 50, 285.
5. For monocyclic azasugars, see e.g.: Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 11, 135; for bicyclic analogues, see e.g.: Michael, J. P. Nat. Prod. Rep. 1995, 12, 535.
6. Kindly supplied by Cerestar, Vilvoorde.
7. (a) Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Chem. Soc., Chem. Commun. 1994, 2147;
8. (b) Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. Tetrahedron Lett. 1994, 35, 9047;
9. (c) Compernolle, F.; Joly, G. J.; Peeters, K.; Toppet, S.; Hoornaert, G.; Kilonda, A.; Babady-Bila, Tetrahedron 1997, 53, 12 739;
10. (d) Kilonda, A.; Compernolle, F.; Hoornaert, G. J. Org. Chem. 1995, 60, 5826.
11. 2C), 128.2, 129.7 (CH tosyl), 134.7, 144.7 (C-ipso tosyl).
12. C-H=161 and 171 Hz are cited for N-methylaziridine by: Kalinowski, H.-O.; Berger, S.; Braun, S. In Carbon-13 NMR Spectroscopy; John Wiley & Sons: Chichester, 1988; p. 441.
13. (a) Duréault, A.; Tranchepain, I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324;
14. (b) Fitremann, J.; Duréault, A.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 1201;
15. (c) Fitremann, J.; Duréault, A.; Depezay, J.-C. Synlett. 1995, 235;
16. (d) McCort, I.; Duréault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717;
17. (e) Fitremann, J.; Duréault, A.; Depezay, J.-C. Synlett. 1995, 235;
18. (f) McCort, I.; Duréault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717;
19. (g) McCort, I.; Duréault, A.; Depezay, J.-C. Tetrahedron Lett. 1998, 39, 4443.
20. Huynh, C.; Derguini-Boumechal, F.; Linstrumelle, G. Tetrahedron Lett. 1979, 20, 1503.
21. Mitsunobu, O. Synthesis 1981, 1.
22. 2C), 126.9, 130.0 (CH tosyl), 136.0, 144.3 (C-ipso tosyl), 169.8 (MeOOC).
23. For C-azadisaccharides, see: (a) Johnson, C. R.; Miller, M. W.; Gedebiowski, A.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991;
24. (b) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991;
25. (c) Frerot, E.; Marquis, C.; Vogel, P. Tetrahedron Lett. 1996, 37, 2023;
26. (d) Johns, B.; Pan, Y.; Elbein, A.; Johnson, C. J. Am. Chem. Soc. 1997, 119, 4856.
27. (a) Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 5311;
28. (b) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599.
29. (a) Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373;
30. (b) Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253.