Studies on the transformation of nitrosugars into iminosugars III: synthesis of (2R,3R,4R,5R,6R)-2-(hydroxymethyl)azepane-3,4,5,6-tetraol and (2R,3R,4R,5R,6S)-2-(hydroxymethyl)azepane-3,4,5,6-tetraol

Tetrahedron Asymmetry

Volumn 21, Issue 1, 2010, Pages 21-26

  Estévez, Amalia M ^a   Soengas, Raquel G ^b   Otero, José M ^a   Estévez, Juan C ^a   Nash, Robert J ^c   Estévez, Ramón J ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF A CORUÑA   (Spain)

^c Phytoquest Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 O BENZYL 6 DEOXY 2,3 DI O ISOPROPYLIDENE 6 NITRO DEXTRO GLYCERO ALPHA MANNOHEPTOFURANOSE; 1 O BENZYL 6 DEOXY 2,3 DI O ISOPROPYLIDENE 6 NITRO GLYCERO ALPHA DEXTRO MANNOHEPTOFURANOSE; 1 O TERT BUTYLDIMETHYLSILYL 6 DEOXY 2,3 DI O ISOPROPYLIDENE 6 NITRO DEXTRO GLYCERO ALPHA DEXTRO MANNOHEPTOFURANOSE; 1 O TERT BUTYLDIMETHYLSILYL 6 DEOXY 2,3 DI O ISOPROPYLIDENE 6 NITRO GLYCERO ALPHA DEXTRO MANNOHEPTOFURANOSE; 2 (HYDROXYMETHYL)AZEPANE 3,4,5,6 TETRAOL; 6 BENZYLOXYCARBONYLAMINO 1 O TERT BUTYLDIMETHYLSILYL 6 DEOXY 2,3 DI O ISOPROPYLIDENE DEXTRO GLYCERO ALPHA DEXTRO MANNOHEPTOFURANOSE; 6 BENZYLOXYCARBONYLAMINO 1 O TERT BUTYLDIMETHYLSILYL 6 DEOXY 2,3 DI O ISOPROPYLIDENE GLYCERO ALPHA DEXTRO MANNOHEPTOFURANOSE; 6 BENZYLOXYCARBONYLAMINO 6 DEOXY 2,3 DI O ISOPROPYLIDENE DEXTRO GLYCERO ALPHA DEXTRO MANNOHEPTOFURANOSE; 6 BENZYLOXYCARBONYLAMINO 6 DEOXY 2,3 DI O ISOPROPYLIDENE GLYCERO ALPHA DEXTRO MANNOHEPTOFURANOSE; ALPHA FUCOSIDE; GLYCOSIDASE INHIBITOR; HEXAHYDRO 6 (HYDROXYMETHYL) 2,2 DIMETHYL 3AH [1,3]DIOXOLO[4,5 C]AZEPINE 7,8 DIOL; HEXAHYDRO 6 (HYDROXYMETHYL) 2,2 DIMETHYL 3AH [1,3]DIOXOLO[4.5 C]AZEPINE 7,8 DIOL; IMINOSUGAR; MANNOSE; NITROSUGAR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; HENRY REACTION; PRIORITY JOURNAL;

EID: 76049110428     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.12.006     Document Type: Article

References (44)

1. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 2000 (1645) 11
2. Lillelund V.H., Jensen H.H., Liang X., and Bols M. Chem. Rev. 102 (2002) 515
3. Compain P., and Martin O.R. Iminosugars: From Synthesis to Therapeutic Applications (2007), John Wiley, Chichester
4. Butters T., Dwek R.A., and Platt F.M. Curr. Top Med. Chem. 3 (2003) 561
5. Mitrakou A., Tountas N., Raptis A.E., Bauer R.J., Schulz H., and Raptis S.A. Diabet. Med. 15 (1998) 657
6. Zitzmann N., Metha A.S., Carrouée S., Butters T.D., Platt F.M., McCauley J., Blumberg B.S., Dwek R.A., and Block T.M. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 11878
7. Asano N. J. Enzyme Inhib. 15 (2000) 215
8. Wu S.-F., Li C.-J., Liao C.-L., Dwek R.A., Zitzmann N., and Lin Y.-L. J. Virol. 76 (2002) 3596
9. Greimel P., Spreitz J., Stütz A.E., and Wrodnigg T.M. Curr. Top. Med. Chem. 3 (2003) 513
10. Jacob G.S. Curr. Opin. Struct. Biol. 5 (1995) 605
11. Inoue S., Tsuruoka T., and Niida T. J. Antibiot. 19 (1966) 288
12. Asano N., Oseki K., Kiuz H., and Matsui K. J. Med. Chem. 37 (1994) 3701
13. Stütz A. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond (1999), Wiley-VCH, Weinheim
14. Paulsen H., and Todt K. Chem. Ber. 100 (1967) 512
15. Andreana P.R., Sanders T., Janczuk A., Warrick J.I., and Wang P.G. Tetrahedron Lett. 43 (2002) 6525
16. Joseph C.C., Regeling H., Zwanenburg B., and Chittenden G.J.F. Tetrahedron 58 (2002) 6907
17. Fuentes J., Gash C., Olano D., Pradera M.A., Repetto P., and Sayago F.J. Tetrahedron: Asymmetry 2002 (1743) 13
18. Dhavale D.D., Chaudhari V.D., and Tilekar J.N. Tetrahedron 44 (2003) 7321 and references cited therein
19. Li H., Blériot Y., Chantereau C., Mallet J.M., Sollogoub M., Zhang Y., García E.R., Vogel P., Barbero J.J., and Sinaÿ P. Org. Biomol. Chem. 2 (2004) 1492
20. Li H., Schuthz C., Favre S., Zhang Y., Vogel P., Sinaÿ P., and Blériot Y. Org. Biomol. Chem. 4 (2006) 1653
21. Marcelo F., He Y., Yuzwa S.A., Nieto L., Jiménez-Barbero J., Sollogoub M., Cocadlo D., Davies G.D., and Blériot Y. J. Am. Chem. Soc. 131 (2009) 5390
22. Li H., Zhang Y., Vogel P., Sinaÿ P., and Blériot Y. Chem. Commun. (2007) 183
23. Li H., Liu T., Zhang Y., Favre S., Bello C., Vogel P., Butters T.D., Oikonomakos N.G., Marrot J., and Blériot Y. ChemBioChem. 9 (2008) 253
24. Li H., Marcelo F., Bello C., Vogel P., Butters T.D., Rauter A.P., Zhang Y., Sollogoub M., and Bleriot Y. Bioorg. Med. Chem. 17 (2009) 5598
25. Martínez-Mayorga K., Medina-Franco J.L., Mari S., Cañada F.J., Rodríguez-García E., Vogel P., Li H., Blériot Y., Sinaÿ P., and Barbero J.J. Eur. J. Org. Chem. 20 (2004) 4119
26. Johnson H.A., and Thomas N.R. Bioorg. Med. Chem. Lett. 12 (2002) 237
27. Soengas R.G., Estévez J.C., Amalia M. Estévez A.M., Fernández F., and Estévez R.J. Carbohydr. Chem. 35 (2009) 1-26
28. Pampín M.B., Fernández F., Estévez J.C., and Estévez R.J. Tetrahedron: Asymmetry 20 (2009) 503
29. Otero J.M., Estévez A.M., Soengas R.G., Estévez J.C., Estévez R.J., Nash R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 19 (2008) 2443
30. Otero J.M., Soengas R.G., Estévez J.C., Estévez R.J., Watking D.J., Evinson E.L., Nash R.J., and Fleet G.W.J. Org. Lett. 9 (2007) 623
31. For other recent synthetic applications from our research group, see:. Fernandez F., Estévez A.M., Estévez J.C., and Estévez R.J. Tetrahedron: Asymmetry 20 (2009) 892
32. Fernández F., Estévez J.C., Sussman F., and Estévez R.J. Tetrahedron: Asymmetry 19 (2008) 2907
33. Otero J.M., Fernández F., Estévez J.C., and Estévez R.J. Tetrahedron: Asymmetry 16 (2005) 4045
34. Otero J.M., Barcia J.C., Estévez J.C., and Estévez R.J. Tetrahedron: Asymmetry 16 (2005) 11
35. Soengas R.G., Pampín M.B., Estévez J.C., and Estévez R.J. Tetrahedron: Asymmetry 15 (2005) 211
36. Soengas R.G., Estévez J.C., and Estévez R.J. Tetrahedron: Asymmetry 14 (2003) 3955
37. Soengas R.G., Estévez J.C., and Estévez R.J. Org. Lett. 5 (2003) 4457
38. (h). Soengas R.G., Estévez J.C., Estévez R.J., and Maestro M.A. Tetrahedron: Asymmetry 2003 (1653) 14
39. Soengas R.G., Estévez J.C., and Estévez R.J. Org. Lett. 5 (2003) 1423
40. Fleet G.W.J., Carpenter N.M., Petursson S., and Ramsden N.G. Tetrahedron Lett. 31 (1990) 409
41. Crystallographic data for the structure of compound 4 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 759124. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax (+44)1223-336-033; e-mail deposit@ccdc.cam.ac.uk).
42. Crystallographic data for the structure of compound 5 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 761857. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax (+44)1223-336-033; e-mail deposit@ccdc.cam.ac.uk).
43. Otero J.M., Estévez A.M., Soengas R.G., Estévez J.C., Nash R.J., Fleet G.W.J., and Estévez R.J. Tetrahedron: Asymmetry 19 (2008) 2443
44. Watson A.A., Nash R.J., Wormald M.R., Harvey D.J., Dealler S., Lees E., Asano N., Kizu H., Kato A., Griffiths R.C., Cairns A.J., and Fleet G.W.J. Phytochemistry 46 (1997) 255