Artículo
Martins Alho, M.A.; D'Accorso, N.B. "Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime" (1999) Journal of Heterocyclic Chemistry. 36(1):177-182
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Abstract:
We report the synthesis of 5-[5'-(1',2':3',4'-di-O-isopropylidene-β-L- arabinopyranosyl)]tetrazole, from 1,2:3,4-di-O-isopropylidene-α-D-galacto- 1,6-hexodialdo-1,5-pyranose oxime via 1,2:3,4-di-O-isopropylidene-α-D- galacturononitrile as intermediate by 1,3-dipolar cycloaddition. We also report the synthesis of 5-methyl- and 5-phenyl-2-[5'-(1',2':3',4',-di-O- isopropylidene-β-L-arabinopyranosyl)]-1,3,4-oxadiazole from the tetrazole derivative. The physical and spectroscopic characterizations of the heterocyclic derivatives as well as the intermediate nitrile and the principal byproduct are described and we discuss its possible formation pathway. We present the preferential conformation in solution using computational calculation and spectroscopic data.
Registro:
| Documento: | Artículo |
| Título: | Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime |
| Autor: | Martins Alho, M.A.; D'Accorso, N.B. |
| Filiación: | Ctro. Invest. de Hidratos de Carbono, Depto. de Quim. Orgánica, Pabellón II, C. P. 1428, Buenos Aires, Argentina |
| Palabras clave: | 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl]tetrazole; 5 methyl 2 [5' (1',2':3',4' di o isoproylidene beta levo arabinosyl] 1,3,4 oxadiazole; 5 phenyl 2 [5' (1',2':3',4' di o isoproylidene beta levo arabinosyl] 1,3,4 oxadiazole; heterocyclic compound; oxadiazole derivative; tetrazole derivative; unclassified drug; article; carbon nuclear magnetic resonance; chemical reaction; chemical structure; organic chemistry; proton nuclear magnetic resonance; synthesis |
| Año: | 1999 |
| Volumen: | 36 |
| Número: | 1 |
| Página de inicio: | 177 |
| Página de fin: | 182 |
| Título revista: | Journal of Heterocyclic Chemistry |
| Título revista abreviado: | J. Heterocycl. Chem. |
| ISSN: | 0022152X |
| CODEN: | JHTCA |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v36_n1_p177_MartinsAlho |
Referencias:
- Valenti, P., Rampa, A., Fabri, G., Giusti, P., Cima, L., (1983) Arch. Pharm., 316, p. 752
- Boivin, J., Hsinec, S., Zard, S.Z., (1995) Tetrahedron, 51, p. 11737
- Ermet, P., Vasella, A., (1991) Helv. Chim. Acta., 74, p. 2043
- Heigthman, T.D., Ermet, P., Vasella, A., Klein, D., (1995) Helv. Chim. Acta., 78, p. 514
- Davis, B., Brandstetter, T.W., Smith, C., Hackett, L., Winchester, B.G., Fleet, G.W.J., (1995) Tetrahedron Letters, 36, p. 7507
- Brandstetter, T.W., Davis, B., Smith, C., Hackett, L., Winchester, B.G., Fleet, G.W.J., (1995) Tetrahedron Letters, 36, p. 7511
- Suman, S.P., Bahel, S.C., (1979) Agric. Biol. Chem., 43, p. 1339
- Mehta, K., Parekh, H., (1988) J. Indian Chem. Soc., 65, p. 521
- Martins Alho, M.A., D'Accorso, N.B., (1997) J. Heterocyclic Chem., 34, p. 1415
- Otegui, L.C., Fascio, M.L., Martins Alho, M.A., D'Accorso, N.B., Thiel, I.M.E., (1990) Anal. Asoc. Quím. Argent., 78, p. 65
- Martins Alho, M.A., Fascio, M.L., D'Accorso, N.B., Thiel, I.M.E., (1995) Carbohydr. Res., 218, p. 223
- Lough, C., Hindsgaul, O., Lemieux, R., (1983) Carbohydr. Res., 120, p. 43
- Horton, D., Nakadate, M., Tronchet, J.M.J., (1968) Carbohydr. Res., 7, p. 56
- Wolfrom, L., Thompson, A., (1931) J. Am. Chem. Soc., 53, p. 622
- Bishop, R., (1993) Comprehensive Org. Synth., 6, p. 261
- Paul F. Schatz, University of Winsconsin - Madison, RAC-COON (Really Awesome Computer Calculation Of Observed NMR Spectra), M. Saunders, Yale University, K. E. Gilbert, and J. J. Gajewski, Indiana University, PMR-Spectrurn Simulator, SERENA Software; Martins Alho, M.A., D'Accorso, N.B., Thiel, I.M.E., (1996) J. Heterocyclic Chem., 33, p. 1339
- Bock, K., Pedersen Advances, C., (1983) Carbohydrate Chemistry and Biochemistry, 41, p. 27
- (1994) MM+ Force Field, PCMODEL for Windows 5.1, , Serena Software
Citas:
---------- APA ----------
Martins Alho, M.A. & D'Accorso, N.B. (1999) . Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime. Journal of Heterocyclic Chemistry, 36(1), 177-182.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v36_n1_p177_MartinsAlho [ ]
---------- CHICAGO ----------
Martins Alho, M.A., D'Accorso, N.B. "Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime" . Journal of Heterocyclic Chemistry 36, no. 1 (1999) : 177-182.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v36_n1_p177_MartinsAlho [ ]
---------- MLA ----------
Martins Alho, M.A., D'Accorso, N.B. "Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime" . Journal of Heterocyclic Chemistry, vol. 36, no. 1, 1999, pp. 177-182.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v36_n1_p177_MartinsAlho [ ]
---------- VANCOUVER ----------
Martins Alho, M.A., D'Accorso, N.B. Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime. J. Heterocycl. Chem. 1999;36(1):177-182.Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v36_n1_p177_MartinsAlho [ ]
