Abstract:
The synthesis of 2-(p-chlorophenyl)-5-[1′2′3′4′5′-penta-O-benzoyl- D-galactopentitol-1-yl]-1,3,4-oxadiazole is described. Its debenzoylation gave an equilibrium mixture of the 1,3,4-oxadiazole derivative without protection of the hydroxyl group and the N-benzoyl-D-galactono-1,4-lactonehydrazone. A similar equilibrium was observed by debenzoylation of 2-phenyl-5-[1′,2′,3′,4′,5′-penta-O-benzoyl-D- galactopentitol-1-yl]-1,3,4-oxadiazole. The 1H, 13C nmr and ms spectra of these compounds are presented.
Registro:
Documento: |
Artículo
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Título: | Synthesis and Debenzoylation Products of Two Perbenzoylated 2-Substituted 5-D-Galactosyl- 1,3,4-oxadiazoles |
Autor: | Cannizzaro, C.E.; Thiel, I.M.E.; D'Accorso, N.B. |
Filiación: | Ctro. Invest. de Hidratos de Carbono, Depto. de Quim. Orgánica, Ciudad Universitaria, Pabellón II, 3o Piso, Buenos Aires, Argentina
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Palabras clave: | 2 (4 chlorophenyl) 5 [1',2',3',5' penta o benzoyl d galactopentitol 1 yl] 1,3,4 oxadiazole; 2 phenyl 5 [1',2',3',4',5' penta o benzoyl d galactopentitol 1 yl] 1,3,4 oxadiazole; oxadiazole derivative; unclassified drug; article; carbon nuclear magnetic resonance; chemical structure; drug conformation; proton nuclear magnetic resonance; synthesis |
Año: | 1998
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Volumen: | 35
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Número: | 2
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Página de inicio: | 481
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Página de fin: | 484
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DOI: |
http://dx.doi.org/10.1002/jhet.5570350238 |
Título revista: | Journal of Heterocyclic Chemistry
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Título revista abreviado: | J. Heterocycl. Chem.
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ISSN: | 0022152X
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CODEN: | JHTCA
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v35_n2_p481_Cannizzaro |
Referencias:
- Sauer, J., Huisgen, R., Sturm, H.J., (1960) Tetrahedron, 11, p. 241
- Huisgen, R., Sauer, J., Sturm, H.J., Markgraf, J., (1960) Chem. Ber., 93, p. 2106
- Huisgen, R., Sauer, J., Sturm, H.J., (1958) Angew. Chem., 70, p. 272
- Seldes, A.M., Gros, E.G., Thiel, I.M.E., Deferrari, J.O., (1976) Carbohydr. Res., 49, p. 49
- Sanchez, A.M.C., D'Accorso, N.B., Thiel, I.M.E., (1989) An. Asoc. Quím. Argent., 77, p. 133
- Martins Alho, M.A., Fascio, M.L., D'Accorso, N.B., Thiel, I.M.E., (1991) Carbohydr. Res., 218, p. 223
- El Khadem, H., Shaban, M., Nassr, M., (1972) Carbohydr. Res., 23, p. 103
- Giri, S., Singh, H., Yadav, L.D.S., (1976) Agric. Biol. Chem., 40, p. 17
- Suman, S.P., Bahel, S.C., (1979) Agric. Biol. Chem., 43, p. 1339
- Ramalinean, T., Deshmukh, A.A., Sattur, P.B., Sheth, U.K., Naik, S.R., (1981) J. Indian Chem. Soc., 58, p. 269
- (1981) Chem. Abstr., 95, pp. 80831w
- Meata, K., Parekh, H., (1988) J. Indian Chem. Soc., 65, p. 521
- Deferrari, J.O., Seldes, A.M., Marzoa, O.G., Thiel, I.M.E., (1971) Carbohydr. Res., 17, p. 237
- Smith, W., (1954) Science, 119, p. 514
Citas:
---------- APA ----------
Cannizzaro, C.E., Thiel, I.M.E. & D'Accorso, N.B.
(1998)
. Synthesis and Debenzoylation Products of Two Perbenzoylated 2-Substituted 5-D-Galactosyl- 1,3,4-oxadiazoles. Journal of Heterocyclic Chemistry, 35(2), 481-484.
http://dx.doi.org/10.1002/jhet.5570350238---------- CHICAGO ----------
Cannizzaro, C.E., Thiel, I.M.E., D'Accorso, N.B.
"Synthesis and Debenzoylation Products of Two Perbenzoylated 2-Substituted 5-D-Galactosyl- 1,3,4-oxadiazoles"
. Journal of Heterocyclic Chemistry 35, no. 2
(1998) : 481-484.
http://dx.doi.org/10.1002/jhet.5570350238---------- MLA ----------
Cannizzaro, C.E., Thiel, I.M.E., D'Accorso, N.B.
"Synthesis and Debenzoylation Products of Two Perbenzoylated 2-Substituted 5-D-Galactosyl- 1,3,4-oxadiazoles"
. Journal of Heterocyclic Chemistry, vol. 35, no. 2, 1998, pp. 481-484.
http://dx.doi.org/10.1002/jhet.5570350238---------- VANCOUVER ----------
Cannizzaro, C.E., Thiel, I.M.E., D'Accorso, N.B. Synthesis and Debenzoylation Products of Two Perbenzoylated 2-Substituted 5-D-Galactosyl- 1,3,4-oxadiazoles. J. Heterocycl. Chem. 1998;35(2):481-484.
http://dx.doi.org/10.1002/jhet.5570350238