A convenient synthesis of N-substituted trihydroxypiperidines from bis- epoxides: Nucleophilic opening of 1,2:4,5-dianhydropentitols

Synlett

Volumn , Issue 2, 2000, Pages 193-196

  Smith, Rachel D ^a   Thomas, Neil R ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Aza sugar; Bis epoxide; Glycosidase inhibitor; Imino sugar; Isofagomine

Indexed keywords

PIPERIDINE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; BINDING AFFINITY; CROSS LINKING; CYCLIZATION; DERIVATIZATION; DRUG SYNTHESIS; EPOXIDATION; REACTION ANALYSIS;

EID: 0033970321     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6499     Document Type: Article

References (27)

1. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond; Stütz, A.E., Ed.; Wiley-VCH: Weinheim, 1999.
2. Bols, M. Acc. Chem. Res. 1998, 31, 1; Legler, G. in Ref. 1 p 41.
3. Bols, M. Acc. Chem. Res. 1998, 31, 1; Legler, G. in Ref. 1 p 41.
4. Ishikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007.
5. Dong, W.; Jesperson, T.; Bols, M.; Skrydstrup, T.; Sierks, M.R. Biochemistry 1996, 35, 2788.
6. Sun, L.; Li, P.; Amankulor, N.; Tang, W.; Landry, D.W.; Zhao, K. J. Org.Chem. 1998, 63, 6472.
7. Robinson, K.M.; Begovic, M.E.; Rhinehart, B.L.; Heinke, E.W.; Ducep, J.-B.; Kastner, P.R.; Marshall, F.N.; Danzin, C. Diabetes 1991, 40, 825.
8. G. Legler in Ref. 1. p 56-59.
9. Lehman, J.; Rob, B. Carbohydrate Res. 1995, 272, C11.
10. Igarashi, Y.; Ichikawa, M.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 1996, 6, 553.
11. Legler, G.; Stutz, A. E.; Immrich, H. Carbohydrate Res. 1995, 272, 17.
12. Paulsen, H.; Steinert, G. Chem. Ber. 1967, 100, 2467.
13. Bernotas, R.C.; Papandreou, G.; Urbach, J.; Ganem, B. Tetrahedron Lett. 1990, 31, 3393.
14. Godskesen, M.; Lundt, I.; Madsen, R.; Winchester, B. Bioorg. Med. Chem. 1996, 4, 1857.
15. Holland, D.; Stoddart, J.F. Carbohydrate Res. 1982, 100, 207.
16. Vidra, I.; Institoris, L.; Simon, K.; Czugler, M.; Csöregh, I. Carbohydrate Res. 1983, 111, 215.
17. Altenbach, H.J.; Merhof, G.F. Tetrahedron: Asymmetry 1996 7, 3087.
18. Chenera, B.; Boehm, J.C.; Dreyer, G.B. Bioorg. Med. Chem. Lett 1991, 1, 219.
19. Schreiber, S.L.; Sammakia, T.; Uehling, D.E. J. Org. Chem. 1989, 54, 15.
20. Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293; Depezay, J.-C. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim 1998; chap. 16.
21. Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293; Depezay, J.-C. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim 1998; chap. 16.
22. A first combinatorial library of azasugar glycosidase inhibitors based on 1-azafagomine has recently been reported; Lohse, A.; Jensen, K.B.; Bols, M. Tetrahedron Lett. 1999, 40, 3033.
23. Kim, D.-K.; Kim, G.; Kim, Y.-W. J. Chem. Soc., Perkin Trans. 1. 1996, 803.
24. Parr, I.B.; Horenstein, B.A. J. Org. Chem. 1997, 62, 7489.
25. Capon R.J.; Barrow, R.A. J. Org. Chem. 1998, 63, 75.
26. For the synthesis of 6-amino-6-deoxy-1,2-3,4-bis-O-isopropylidene-D-galactose see J.M. Garcia Fernandez, C.O. Mellet, J. Fuentes J. Org. Chem. 1993, 58, 5192.
27. 2).