Synthesis of C-glycosyl isoxazoles and branched-chain enuloses from 2,3-O-isopropylidene-D-glyceraldehyde

Article abstract of DOI:10.1080/07328309808002357

The synthesis of 5-glycosyl isoxazoles with 3-alkyl-, 3-aryl, 3,4-dialkyl, 3-aryl-4-alkyl or 3-alkyl-4-bromo substituents is reported. Deoxyenuloses were obtained from reaction of 2,3-O-isopropylidene-D-glyceraldehyde and several phosphorus ylides, which contain a carbonyl group, by a Wittig reaction. C-glycosyl α,β-unsaturated ketones were obtained, with the polyhydroxylate chain lengthened by two or three carbon atoms. In the second phase the ketones were transformed into the corresponding C-glycosyl α,β-unsaturated ketoximes, leading to the C-glycosyl isoxazoles, which were converted into the title compounds via removal of the isopropylidene group of suitably protected carbohydrates. The solubility of the synthetized C-glycosyl isoxazoles were modified by free hydroxyl groups in such a way that their behaviour against certain viruses and their potential antiviral activity could be studied.

Full text of DOI:10.1080/07328309808002357

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Journal of Carbohydrate Chemistry
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Synthesis of C-Glycosyl Isoxazoles and
Branched-Chain Enuloses From 2,3-O-
Isopropylidene-D-Glyceraldehyde
J. M. Báñez Sanz a , J. A. López Sastre a , M. R. Patiño Molina a & C.
Romero-Ávila García a
a Departamento de Química Orgánica , Instituto de Investigación y
Desarrollo Tecnológico Industrial. E.T.S. de Ingenieros Industriales.
Universidad de Valladolid , 47071, Valladolid, Spain
Published online: 23 Aug 2006.
To cite this article: J. M. Báñez Sanz , J. A. López Sastre , M. R. Patiño Molina & C. Romero-Ávila
García (1998) Synthesis of C-Glycosyl Isoxazoles and Branched-Chain Enuloses From 2,3-O-
Isopropylidene-D-Glyceraldehyde, Journal of Carbohydrate Chemistry, 17:9, 1331-1350, DOI:
10.1080/07328309808002357
To link to this article: http://dx.doi.org/10.1080/07328309808002357
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