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Volumn 59, Issue 2, 2003, Pages 547-571

Synthesis of ketosyl spiro-isoxazolidine by 1,3-dipolar cycloaddition of 1-methylenesugars with nitrones - A new access to C-glycosyl amino acids

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYLENESUGAR; ALKENE; AMINO ACID; CARBOXYLIC ACID DERIVATIVE; DISACCHARIDE; GLYCOSIDE; ISOXAZOLIDINE DERIVATIVE; LEWIS ACID; NITRONE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

EID: 0037347466     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-s52     Document Type: Article
Times cited : (35)

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    • For the recent syntheses of spiro-ketals, see: (a) A. Dondoni, A. Marra, M.-C. Scherrmann, and V. Bertolasi, Chem. Eur. J., 2001, 7, 1371; (b) X. Li, H. Takahashi, H. Ohtake, M. Shiro, and S. Ikegami, Tetrahedron, 2001, 57, 8053; (c) J. M. Benito, M. Gomez-Garcia, C. O. Mellet, J. M. G. Fernandez, and J. Defaye, Org. Lett., 2001, 3, 549 and the cited therein; (d) R. Caputo, A. Guaragna, G. Palumbo, S. Pedatella, and F. Solla, Eur. J. Org. Chem., 2002, 534; (e) C. Hamdouchi, C. Jaramillo, J. Lopez-Prados, and A. Rubio, Tetrahedron Lett., 2002, 43, 3875; (f) M. Manley-Harris and G. N. Richards, Dihexulose Dianhydrides, in Adv. Carbohydr. Chem. Biochem., Vol. 52, ed. by D. Horton, Academic Press, San Diego, 1997, pp. 207-266.
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    • Besides the 1,3-dipolar cycloadditions, the neucleophilic additions to nitrones have been also widely used in organic synthesis. See recent reviews: (a) P. Merino, S. Franco, F. L. Merchan, and T. Tejero, Synlett, 2000, 442;
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    • To the best of our knowledge, only one example was reported on the 1,3-dipolar cycloaddition reaction of 1-methylsugar with a nitrile oxide to give a single spiro isooxazoline in the α-stereospecific way. See: T. V. RajanBabu and G. S. Reddy, J. Org. Chem., 1986, 51, 5458.
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    • note
    • LOMD for each compound of 3a and 4a, and their diastereomers (3s) and (4s) was continued until around 5,000 conformers were generated. Although the steps in LOMD were not enough for the determination of the molecule conformations, the energies among the first twenty lowest energy conformers of compounds (3a) and (4a) were almost same for each molecule.
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