Synthesis of 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol, a novel analogue of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, via an Amadori rearrangement of 5-azido-5-deoxy-D-glucofuranose

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5463-5466

  Wrodnigg, Tanja M ^a   Stütz, Arnold E ^a   Withers, Steven G ^b  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 1,2,5 TRIDEOXY 2,5 IMINO DEXTRO MANNITOL; GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; HYDROGENATION; REACTION ANALYSIS;

EID: 18344415504     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01198-2     Document Type: Article

References (8)

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2. Legler, G.; Lüllau, E.; Kappes, E.; Kastenholz, F. Biochim. Biophys. Acta 1991, 1080 (2), 89-95.
3. Legler, G.; Korth, A.; Berger, A.; Ekhart, C. W.; Gradnig, G.; Stütz, A. E. Carbohydr. Res. 1993, 250, 67-77.
4. Dax, K.; Gaigg, B.; Grassberger, V.; Kölblinger, B.; Stütz, A. E. J. Carbohydr. Chem. 1990, 9, 479-499.
5. Berger, A.; de Raadt, A.; Gradnig, G.; Grasser, M.; Löw, H.; Stütz, A. E. Tetrahedron Lett. 1992, 33, 7125-7128.
6. Hodge, J. E. Adv. Carbohydr. Chem. 1955, 10, 169-205 and ref. cited there.
7. ,2 7.0 Hz, H-1'), 3.11-2.93 (m, 2 H, H-2, H-5).
8. Takaoka, Y.; Kajimoto, T.; Wong, C.-H. J. Org. Chem. 1993, 58, 4809-4812.