Synthesis of (+)-azafagomine from D-xylose

Synlett

Volumn , Issue 6, 1999, Pages 701-704

  Ernholt, Bettina V ^a   Thomsen, Ib B ^a   Jensen, Kenneth B ^b   Bols, Mikael ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

Azasugar; Glycosidase inhibitor; Hydrazine; Reductive amination

Indexed keywords

AZAFAGOMINE; GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG; XYLOSE;

AMINATION; ARTICLE; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033032553     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2716     Document Type: Article

References (20)

1. Legler, G. Advan. Carbohydr. Chem. Biochem. 1990, 48, 319.
2. Fleet, G. W.; Winchester, B. Glycobiology 1992, 2, 199.
3. Lehmann, J.; Rob, B. Tetrahedron: Asymmetry 1994, 5, 2255.
4. Cottaz, S.; Brimacombe, J. S.; Ferguson, M. A. J. Carbohydr. Res. 1993, 247, 341.
5. Sears, P.; Wong, C. -H. Chem. Commun. 1998, 1161.
6. Ermert, P.; Vasella, A.; Weber, A.; Rupitz, K.; Withers, S. G. Carbohydr. Res. 1993, 250, 113.
7. Martin, O. R.; Saavedra, O. M. Tetrahedron Lett. 1995, 36, 799.
8. Siriwardena, A. H.; Chiaroni, A.; Riche, C.; El-Daher, S.; Winchester, B.; Grierson, D. S. J. Chem. Soc. Chem. Commun. 1992, 1531.
9. Schmidt, R. R.; Dietrich, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 1328.
10. Ganem, B. Acc. Chem. Res. 1996, 29, 340.
11. Bols, M.; Hazell, R. G.; Thomson, I. Chem. Eur. J. 1997, 3, 940.
12. 3): δ 7.3 (m, 15H, PhH), 6.2 (bs, 1H, BocNH), 4.4-4.7 (m, 6H, Bn's), 4.3 (bs, 2H, OH, NH)
13. Stroh, H. -H.; Arnold, A.; Schamow, H. -G. Chem. Ber. 1964, 98, 1404.
14. Zinner, H.; Brandhoff, H.; Schmandke, H.; Kristen, H.; Huun, R. Chem. Ber. 1959, 92, 151.
15. Zinner, H.; Wessely, K.; Kristen, H. Chem. Ber, 1959, 92, 1618.
16. There are several literature examples of reductive amination of amides: Parr, I. B.; Horenstein, B. A. J. Org. Chem. 1997, 7,7489. Fache, F.; Jaquot, L.; Lemaire, M. Tetrahedron Lett. 1994, 35, 3313.
17. There are several literature examples of reductive amination of amides: Parr, I. B.; Horenstein, B. A. J. Org. Chem. 1997, 7,7489. Fache, F.; Jaquot, L.; Lemaire, M. Tetrahedron Lett. 1994, 35, 3313.
18. For a procedure see Barbaud, C.; Bols, M.; Lundt, I.; Sierks, M. R. Tetrahedron 1995, 51, 9063.
19. Formation of a 6-membered ring can occur when a trans-fused acetonide is present, see Dureault, A.; Tranchepain, I.; Depezay, J. -C. J. Org. Chem, 1989, 54, 5324-5330. However in those cases the substitution occured at a primary center and not a to the acetonide.
20. Fleet, G. W. J.; Nicholas, S. J.; Smith, P. W.; Evans, S. V.; Fellows, L. E.; Nash, R. J. Tetrahedron Lett. 1985, 26, 3127.