Synthesis of O-unprotected glycosyl selenoureas. A new access to bicyclic sugar isoureas

Tetrahedron Letters

Volumn 45, Issue 21, 2004, Pages 4081-4084

  Fernández Bolaños, José G ^a   López, Óscar ^a   Ulgar, Víctor ^a   Maya, Inés ^a   Fuentes, José ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

Hydrogen peroxide; Isoselenocyanates; Isoureas; Selenium; Selenoureas; Triphosgene

Indexed keywords

1,4 PHENYLENE DIISOSELENOCYANATE; AMINOGLYCOSIDE DERIVATIVE; CARBOHYDRATE DERIVATIVE; CYANIC ACID DERIVATIVE; FORMAMIDE DERIVATIVE; OXYGEN PEROXIDE; PEROXIDE; PHENYLISOSELENOCYANATE; PHOSGENE; PYRIDINE; SELENIUM; TRIETHYLAMINE; TRIPHOSGENE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; LIQUID; SYNTHESIS;

EID: 2342596537     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.143     Document Type: Article

References (45)

1. Wirth T. Organoselenium Chemistry: Modern Developments in Organic Synthesis. 2000;Springer, Berlin
2. Nicolaou K.C., Fylaktakidou K.C., Mitchell H.J., Van Delft F.L., Rodríguez R.M., Conley S.R., Jin Z. Chem. Eur. J. 6:2000;3166-3185
3. Petragnani N., Stefani A., Valduga C.J. Tetrahedron. 57:2001;1411-1448
4. Koketsu M., Yang H.O., Kim Y.M., Ichihashi M., Ishihara H. Org. Lett. 3:2001;1705-1707
5. Birringer M., Pilawa S., Flohé L. Nat. Prod. Rep. 19:2002;693-718
6. Whanger P.D. Br. J. Nutr. 91:2004;11-28
7. Johnston B.D., Ghavami A., Jensen M.T., Svensson B., Pinto B.M. J. Am. Chem. Soc. 124:2002;8245-8250
8. Arca M., Demartin F., Devillanova F.A., Isaia F., Lelj F., Lippolis V., Verani G. Can. J. Chem. 78:2000;1147-1157
9. Zhou Y., Linden A., Heimgartner H. Helv. Chim. Acta. 83:2000;1576-1598
10. Atanassov P.K., Linden A., Heimgartner H. Helv. Chim. Acta. 86:2003;3235-3243
11. Koketsu M., Ishihara H. Curr. Org. Chem. 7:2003;175-185
12. Fernández-Bolaños J.G., Skydstrup T., López-Castro A., Diánez M.J., Estrada M.D. Carbohydr. Res. 237:1992;303-311
13. Zhou Y., Denk K. Tetrahedron Lett. 44:2003;1295-1299
14. Koketsu M., Takakura N., Ishihara H. Synth. Commun. 32:2002;3075-3079
15. Keil D., Hartmann H. Phosphorus, Sulfur, Silicon and the Related Elements. 152:1999;169-184
16. Henriksen L. Synthesis. 1982;773-776
17. Takikawa Y., Watanabe H., Sasaki R., Shimada K. Bull. Chem. Soc. Jpn. 67:1994;876-878
18. Koketsu M., Suzuki N., Ishihara H. J. Org. Chem. 64:1999;6473-6475
19. Fujiwara S.-I., Kambe N., Sonoda N. Back T.G. Organoselenium Chemistry: A Practical Approach. 1999;223-240 Oxford University Press
20. Ichikawa Y., Nishiyama T., Isobe M. J. Org. Chem. 66:2001;4200-4205
21. Nishiyama T., Ichikawa Y., Isobe M. Synlett. 2003;47-50
22. Maya I., López O., Maza S., Fernández-Bolaños J.G., Fuentes J. Tetrahedron Lett. 44:2003;8539-8543
23. Heck R., Marsura A. Tetrahedron Lett. 45:2004;281-284
24. García Fernández J.M., Ortiz Mellet C. Adv. Carbohydr. Chem. Biochem. 55:1999;35-135
25. Sansone F., Chierici E., Casnati A., Ungaro R. Org. Biomol. Chem. 1:2003;1802-1809
26. Patel A., Lindhorst T.K. Eur. J. Org. Chem. 2002;79-86
27. Witczak Z.J. Tetrahedron. 41:1985;4781-4785
28. Wirth T. Tetrahedron. 55:1999;1-28
29. 2 (2 mL) for a period of 1 h. After the addition, it was refluxed for 2.5 h and then, selenium powder (3.0 mmol) was added. The resulting mixture was refluxed for other 4-7 h; conventional work-up and column chromatography afforded isoselenocyanates 6-10
30. Barton D.H.R., Parekh S.I., Tajbakhsh M., Theodorakis E.A., Tse C.-L. Tetrahedron. 50:1994;639-654
31. Cotarca L., Eckert H. Phosgenations - A Handbook. 2003;Wiley-VCH, Weinheim
32. Cotarca L., Delogu P., Nardelli A., Šunji V. Synthesis. 1996;553-576
33. Morel G., Marchand E., Sinbandhit S., Carlier R. Eur. J. Org. Chem. 2001;655-662
34. Efraty A., Feinstein I., Wackerle L., Goldman A. J. Org. Chem. 45:1980;4059-4061
35. Su W.K., Liang X.R. J. Indian Chem. Soc. 80:2003;645-647
36. + 385.0279, found 385.0267
37. + 303.0957, found 303.0963
38. Mukaiyama T. Angew. Chem., Int. Ed. Engl. 18:1979;707-721
39. Takeda T., Mukaiyama T. Chem. Lett. 1980;163-166
40. Kim T.H., Lee N., Lee G.-J., Kim J.N. Tetrahedron. 57:2001;7137-7141
41. Almaraz M., Raposo C., Martin M., Caballero M.C., Moran J.R. J. Am. Chem. Soc. 120:1998;3516-3517
42. Treppendahl S. Acta Chem. Scand. B29:1975;385-388
43. López O., Maya I., Fuentes J., Fernández-Bolaños J.G. Tetrahedron. 60:2004;61-72
44. Shiozaki M., Mochizuki T., Hanzawa H., Haruyama H. Carbohydr. Res. 288:1996;99-108
45. Tapiero H., Townsend D.M., Tew K.D. Biomed. Pharmacother. 57:2003;134-144