A Formal Total Synthesis of Deoxynojirimycin from D-Glucitol

Journal of the Brazilian Chemical Society

Volumn 14, Issue 5, 2003, Pages 822-827

  Braga, Raquel M ^a   Kato, Lucilia ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

D glucitol; Deoxynojirimycin; Glycosidase inhibitors; Isopropylidene derivatives

Indexed keywords

1,5 DIDEOXY 1,5 DIAMINE 2,3 O ISOPROPYLIDENE 6 SILYL DEXTRO GLUCITOL; DEOXYNOJIRIMYCIN; EPOXIDE; PROPANE; SORBITOL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; PRECURSOR; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING OPENING; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0242437866     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50532003000500019     Document Type: Article

References (25)

1. MacNaught, A.D.; Carbohydr. Res. 1997, 297, 1.
2. Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y.; J. Am. Chem. Soc. 1998, 120, 3007.
3. Look, G.C.; Fotsch, C.H.; Wong, C-H.; Acc. Chem. Res. 1993, 26, 182.
4. Merrer, Y.L.; Poitout, L.; Depezay, J-C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M-J.; Bioorg. Med. Chem. 1997, 5, 510.
5. Xu, Y-M.; Zhou, W-S.; Tetrahedron Lett. 1996, 37, 1461.
6. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G.J.; J. Chem. Soc. Chem. Commun. 1994, 2147.
7. Hughes, B.; Rudge, J.; Nat. Prod. Rep. 1994, 135.
8. Kilonda, A.; Compernolle, F.; Peeters, K.; Joly, G. J.; Toppet, S.; Hoornaert, G.J.; Tetrahedron 2000, 56, 1005.
9. Paulsen, H.; Sangster, I; Heynes, K.; Chem. Ber. 1967, 100, 802.
10. Kinast, G.; Schedel, M.; Angew Chem. Int. Ed. Eng. 1981, 20, 805.
11. Behling, J.; Medich, J.R.; Scaros, M.G.; Prunier, M.; Weier, R. M.; Khanna, I.; Synth. Commun 1991, 21, 1383.
12. Setoi, H.; Takeno, H.; Hashimoto, M.; Chem. Pharm. Bull 1986, 34, 2642.
13. Setoi, H.; Takeno, H.; Hashimoto, M.; Tetrahedron Lett. 1985, 26, 4617.
14. Doane, W.M.; Shasha, B.S.; Russel, C.R.; Rist, C.E.; J. Org. Chem. 1967, 32, 1080.
15. Matos, C. R. R.; Lopes, R. S. C.; Lopes, C. C.; Synthesis 1999, 4, 571.
16. Somfai, P.; Marchand, P.; Torsell, S.; Lindström, U. M.; Tetrahedron 2003, 59, 1293.
17. Han, H.; Tetrahedron Lett. 2003, 44, 1567.
18. Comins, D.L.; Fulp, A.B.; Tetrahedron Lett. 2001, 42, 6839.
19. Kato, L.; M. Sc Dissertation, Universidade Estadual de Campinas, Brazil, 1996.
20. th ed., Wiley: New York, 1991
21. Kato, L.; Braga, R. M.; Mag. Res. Chem. 1999, 37, 447.
22. Reactivos de Coloración para Cromatografía en Capa Fina y en Papel, E. Merck, Darmstadt: Germany, 1972, p. 92.
23. rd ed., Pergamon Press:Oxford, 1988
24. Kuzsmann, J.; Sohar, P.; Carbohydr. Res. 1979, 74, 187.
25. Kuzsmann, J.; Kiss, L.; Carbohydr. Res. 1986, 153, 45.