Bicyclic azasugars containing a glycosidic heteroatom: D-xylose analogues

Tetrahedron

Volumn 55, Issue 22, 1999, Pages 6759-6770

  Berges, David A ^a   Fan, Jianmei ^a   Devinck, Sylvie ^a   Liu, Nannan ^a   Dalley, N Kent ^a  

^a BRIGHAM YOUNG UNIVERSITY   (United States)

Author keywords

Aza compounds; Carbohydrate mimetics; Enzyme inhibitors; X Ray crystal structures

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLYCOSIDE; XYLOSE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; CYCLIZATION; ISOMER; MOLECULAR MODEL; MOLECULAR STABILITY; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033612105     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00335-X     Document Type: Article

References (20)

1. de Raadt, A.; Ekhart, C. W.; Ebner, M.; Stütz, A. E. Topics Curr. Chem. 1997, 187, 157-186.
2. Williams, J. M. In Glycopeptides and Related Compounds. Synthesis, Analysis, and Applications; Large, D. G.; Warren, C. D., Eds.; Marcel Dekker: New York, 1997; pp. 505-539.
3. Inouye, S.; Tsuruoka, T.; Ito, T.; Niida, T. Tetrahedron 1968, 23, 2125-2144.
4. Legler, G.; Jülich, E. Carbohydr. Res. 1984, 128, 61-72.
5. Miyake, Y.; Ebata, M. J. Antibiot. 1987, 40, 122-123.
6. Kayakiri, H.; Takase, S.; Shibata, T.; Okamoto, M.; Terano, H.; Hashimoto, M.; Tada, T.; Koda, S. J. Org. Chem. 1989, 54, 4015-4016.
7. Yoon, H.; King, S. B.; Ganem, B. Tetrahedron Lett. 1991, 32, 7199-7202.
8. Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661-5666.
9. Marek, D.; Wadouachi, A.; Uzan, R.; Beaupere, D.; Nowogrocki, G.; Laplace, G. Tetrahedron Lett. 1996, 37, 49-52.
10. Berges, D. A.; Ridges, M. D.; Dalley, N. K. J. Org. Chem. 1998, 63, 391-392.
11. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097-5104.
12. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons, Inc.: New York; 1994; pp. 696-697.
13. Lemieux, R. U.; Koto, S.; Voisin, D. In Anomeric Effect, Origin and Consequences; Szarek, W. A.; Horton, D., Eds.; ACS Symposium Series 87, American Chemical Society: Washington, DC, 1979, pp. 17-29.
14. 8,9
15. The preparations of 15 and 17 have been described, but the latter product was not characterized. Tamura, T.; Kuneida, T.; Takizawa, T. J. Org. Chem. 1974, 39, 38-44.
16. Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer: New York; 1983; pp. 22-23.
17. 6 = 1.458Å.
18. 6 = 1.505Å.
19. 13C NMR signals at 67.9 and 62.8 ppm distinguish the minor compound from all the bicyclic azasugars we have prepared and characterized but correspond more closely with the 66.4 and 62.9 ppm reported for 1,4-dideoxy-1,4-imino-L-arabinitol, a monocyclic analogue of compound 23 reported in Nash, R. J.; Williams, J. M., Bell, E. A. Phytochemistry 1985, 24, 1620-1622.
20. Peak position obtained from cross peaks of COSY spectrum.