Synthesis, configurational and conformational studies of six amino sugar precursors formed by [3+2]cycloaddition of alkylnitrile oxides to enone sugars

Synlett

Volumn , Issue 9 SPEC. ISS., 2003, Pages 1358-1360

  De Freitas Filho, João R ^a,b   Cottier, Louis ^a   Srivastava, Rajendra M ^b   Sinou, Denis ^a  

^a UNIVERSITÉ LYON 1   (France)

^b FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

Author keywords

Heterobicyclic system; Montmorillonite K 10; NMR spectroscopy; Sugar enones; Tri O acetyl D glucal

Indexed keywords

ACETAL; ACETONITRILE; ALPHA,BETA UNSATURATED SUGAR ENONE; AMINOSUGAR; GLUCOSE; HETEROCYCLIC COMPOUND; ISOXAZOLINOPYRANOSIDE; MONTMORILLONITE; NITRILE; OXIDE; PROPIONITRILE; SUGAR ACID; SUGAR ENONE; TRI O ACETYL DEXTRO GLUCAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRECURSOR; SYNTHESIS;

EID: 0037765516     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40354     Document Type: Article

References (16)

1. Gallos, J. K.; Koumbis, A. E.; Xiraphari, V. P.; Dellios, C. C.; Coutouli-Argyropoulou, E. Tetrahedron 1999, 55, 5167.
2. Nataka, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363.
3. (a) Kobayashi, Y.; Miyazaki, H.; Shioazaki, M. J. Am. Chem. Soc. 1992, 114, 10065.
4. (b) Kobayashi, Y.; Miyazaki, H.; Shioazaki, M. J. Org. Chem. 1994, 59, 813.
5. Gallos, J. K.; Koftis, T. V. J. Chem. Soc., Perkin Trans. 1 2001, 415.
6. Srivastava, R. M.; De Souza, A. M. A.; Da Silva, L. P.; De Freitas Filho, J. R.; Hallwass, F.; Doboszewski, B. J. Braz. Chem. Soc. 2002, 13, 158.
7. De Freitas Filho, J. R.; Srivastava, R. M.; Soro, Y.; Cottier, L.; Descotes, G. J. Carbohydr. Chem. 2001, 20, 561.
8. Toshima, K.; Ishizuka, T.; Matsuo, G.; Nataka, M. Synlett 1995, 306.
9. Fraser-Reid, B.; Mclean, A.; Usherwood, E. W.; Yunker, M. Can. J. Chem. 1970, 48, 2877; and references cited therein.
10. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
11. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339.
12. Srivastava, R. M.; Clapp, L. B. J. Heterocycl. Chem. 1968, 5, 61.
13. Hassner, A.; Dahren, W. J. Org. Chem. 1990, 55, 5505.
14. 3Si).
15. Srivastava, R. M.; Carthy, B. J.; Fraser-Reid, B. Tetrahedron Lett. 1974, 2175.
16. The elemental analyses of all new compounds, viz. 5a-c, 6a-c and 7d-i agreed with the proposed structures.