Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration

Tetrahedron Asymmetry

Volumn 17, Issue 13, 2006, Pages 2006-2014

  Le Bouc, Géraldine ^a   Thomassigny, Christine ^a   Greck, Christine ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYHOMONOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN DERIVATIVE; 1,5,6 TRIDEOXY 1,5 IMINO DEXTRO ALLOHEPTITOL; 1,5,6 TRIDEOXY 1,5 IMINOTALOHEPTITOL; ESTER DERIVATIVE; FURAN DERIVATIVE; GLUCOSE DERIVATIVE; IMINO ACID; OXOACID; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG SCREENING; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 33746963920     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.07.022     Document Type: Article

References (43)

1. For some reviews, see:. Tatsuta K. In: Chapleur Y. (Ed). Carbohydrate Mimics (1998), Wiley-VCH, Weinheim 283
2. Fechter M.H., Stütz A.E., and Tauss A. Curr. Org. Chem. 3 (1999) 269-285
3. For recent articles, see:. Weintraub P.M., Sabol J.S., Kane J.M., and Borcherding D.R. Tetrahedron 59 (2003) 2953-2989
4. Afarinkia K., and Bahar A. Tetrahedron: Asymmetry 16 (2005) 1239-1287
5. Pearson M.S.M., Mathé-Allainmat M., Fargeas V., and Lebreton J. Eur. J. Org. Chem. (2005) 2159-2191
6. Inouye S., Tsuruoka T., Ito T., and Niida T. Tetrahedron 24 (1968) 2125-2144
7. Zhou J.-M., Zhou J.-H., Meng Y., and Chen M.-B. J. Chem. Theor. Comput. 2 (2006) 157-165
8. Lillelund V.H., Jensen H.H., Liang X., and Bols M. Chem. Rev. 102 (2002) 515-553 and references cited therein
9. Sinnott M.L. In: Pike M.I., and Williams A. (Eds). Enzyme Mechanisms (1987), Royal Soc. Chem., London 259
10. Stütz A.E. Angew. Chem., Int. Ed. 35 (1996) 1926-1928
11. Lai E.C.K., Morris S.A., Street I.P., and Withers S.G. Bioorg. Med. Chem. 4 (1996) 1929-1937
12. Blake C.C.F., Johnson L.N., Mair G.A., North A.T.C., Phillips D.C., and Sharma V.R. Proc. R. Soc. London Ser. B 167 (1967) 378-388
13. Fleet G.W.J. Tetrahedron Lett. 26 (1985) 5073-5076
14. Ganem B., and Papandreou G. J. Am. Chem. Soc. 113 (1991) 8984-8985
15. Kajimoto T., Liu K.K.-C., Pederson R.L., Zhong Z., Ichikawa Y., Porco Jr. J.A., and Wong C.-H. J. Am. Chem. Soc. 113 (1991) 6187-6196
16. Jespersen T.M., Bols M., Sierks M.R., and Skrydstrup T. Tetrahedron 50 (1994) 13449-13460 and references cited therein
17. Kilonda A., Compernolle F., Toppet S., and Hoornaert G.J. Tetrahedron Lett. 35 (1994) 9047-9050
18. Compernolle F., Joly G., Peeters K., Toppet S., and Hoornaert G. Tetrahedron 53 (1997) 12739-12754
19. Shilvock J.P., Hsia K.Y., Nash R.J., Lloyd J.D., Winters A.L., Asano N., and Fleet G.W.J. Tetrahedron: Asymmetry 9 (1998) 4157-4164
20. Rassu G., Pinna L., Spanu P., Culeddu N., Casiraghi G., Fava G.G., Ferrari M.B., and Pelosi G. Tetrahedron 48 (1992) 727-742
21. Chen Y., and Vogel P. J. Org. Chem. 59 (1994) 2487-2496
22. Baudat A., Picasso S., and Vogel P. Carbohydr. Res. 281 (1996) 277-284
23. Picasso S., Chen Y., and Vogel P. Carbohydr. Lett. 1 (1994) 1-8
24. Lundt I., and Madsen R. Synthesis (1995) 787-794
25. Szolcsányi P., Gracza T., Koman M., Prónayová N., and Liptaj T. Tetrahedron: Asymmetry 11 (2000) 2579-2597
26. Szolcsányi P., Gracza T., Koman M., Prónayová N., and Liptaj T. Chem. Commun. (2000) 471-472
27. Saha N.N., Desai V.N., and Dhavale D.D. Tetrahedron 57 (2001) 39-46
28. Patil N.T., Tilekar J.N., and Dhavale D.D. J. Org. Chem. 66 (2001) 1065-1074
29. Dhavale D.D., Matin M.M., Sharma T., and Sabharwal S.G. Bioorg. Med. Chem. 11 (2003) 3295-3305
30. Thomassigny C., Barroso M.T., and Greck C. Lett. Org. Chem. 2 (2005) 316-318
31. Desai V.N., Saha N.N., and Dhavale D.D. Chem. Commun. (1999) 1719-1720
32. Achmatowicz M., and Hegedus L.S. J. Org. Chem. 69 (2004) 2229-2234
33. Herdeis C., and Schiffer T. Tetrahedron 52 (1996) 14745-14756
34. Thomassigny C., and Greck C. Tetrahedron: Asymmetry 15 (2004) 199-201
35. Kim K.S., Song Y.H., Lee B.H., and Hahn C.S. J. Org. Chem. 51 (1986) 404-407
36. Raghavendra Swamy N., and Venkateswarlu Y. Tetrahedron Lett. 43 (2002) 7549-7552
37. Brooks D.W., Lu L.D.L., and Masamune S. Angew. Chem., Int. Ed. Engl. 1 (1979) 72-74
38. Genet J.P., Ratovelomanana-Vidal V., Caño de Andrade C., Pfister X., Guerreiro P., and Lenoir J.Y. Tetrahedron Lett. 36 (1995) 4801-4804
39. Ratovelomanana-Vidal V., and Genet J.P. Organomet. Chem. 567 (1998) 163-171
40. Yoshikawa M., Okaichi Y., Cha B.C., and Kitagawa I. Tetrahedron 46 (1990) 7459-7470
41. Matulic-Adamic J., Haeberli P., and Usman N. J. Org. Chem. 60 (1995) 2563-2569
42. Dhavale D.D., Tagliavini E., Trombini C., and Umani-Ronchi A. J. Org. Chem. 54 (1989) 4100-4105
43. In: Aramarego W.L.F., and Perrin D.D. (Eds). Purification of Laboratory Chemicals. 4th ed. (1996), Butterwoth Heinemann