New entry to pyrrolidine homoazasugars: Conversion of D-arabinose into 2,5-anhydro-2,5-imino-D-glucitol via aminohomologation

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9375-9378

  Dondoni, Alessandro ^a   Perrone, Daniela ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

2 Lithiothiazole; Homoazasugars; Sugar nitrones

Indexed keywords

ARABINOSE DERIVATIVE; PYRROLIDINE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; REDUCTION; STEREOCHEMISTRY;

EID: 0033601406     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01987-5     Document Type: Article

References (16)

1. Dondoni, A.; Franco, S.; Junquera, P.; Merchán, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505-520.
2. (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496.
3. (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F. L.; Merino, P.; Tejero; T. J. Org. Chem. 1997, 62, 5497-5507.
4. Fleet, G. W. J.; Smith, P. W. Tetrahedron Lett. 1985, 26, 1469-1472.
5. (a) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777-6780.
6. (b) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185.
7. Liu, K. K.-C.; Kajimoto, T.; Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280-6289.
8. (a) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182-190.
9. (b) Iminosugarsas Glycosidase Inhibitors; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1998.
10. Barker, R.; Fletcher Jr., H. G. J. Org. Chem. 1961, 26, 4605-4609.
11. Dondoni, A.; Perrone, D.; Rinaldi, M. J. Org. Chem. 1998, 63, 9252-9264.
12. 2O), 7.00-7.10 (m, 2H), 7.17 (d, 1H, J=3.2 Hz), 7.20-7.40 (m, 18H), 7.67 (d, 1H, J=3.2 Hz).
13. (a) Nagai, M.; Gaudino, J. J.; Wilcox, C. S. Synthesis 1992, 163-168.
14. (b) Lay, L.; Nicotra, F.; Paganini, A.; Pangrazio, C.; Panza, L. Tetrahedron Lett. 1993, 34, 4555-4558.
15. Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277.
16. Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849-3855.