Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs
Methanolysis of 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone gave methyl 3-bromo-3-deoxy-2,4,6-tri-O-benzoyl-α-D-ribo-hex-2-ulofuranosonate (3) and the anomeric mixture of the analogous 4,6-di-O-benzoyl derivative, having HO-2 free. Compound 3 was subjected to debromination with tri...
Guardado en:
| Autor principal: | |
|---|---|
| Otros Autores: | |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2000
|
| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 06537caa a22009617a 4500 | ||
|---|---|---|---|
| 001 | PAPER-2260 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203139.0 | ||
| 008 | 190411s2000 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0034613025 | |
| 024 | 7 | |2 cas |a 3-deoxyhexulose, 6196-57-2; Furans; galactonic acid, 13382-27-9; Gluconates; Ketoses; Sugar Acids | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a CRBRA | ||
| 100 | 1 | |a Di Nardo, C. | |
| 245 | 1 | 0 | |a Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs |
| 260 | |c 2000 | ||
| 270 | 1 | 0 | |m Varela, O.; Departamento de Qumica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon II, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: varela@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Ashwell, G., Wahba, A.J., Himckan, J., (1960) J. Biol. Chem., 235, pp. 1559-1565 | ||
| 504 | |a Condemine, G., Hugouvieux-Cotte-Pattat, N., Robert-Baudouy, J., (1986) J. Bacteriol., 165, pp. 937-940 | ||
| 504 | |a Claus, D., (1965) Biochem. Biophys. Res. Commun., 20, pp. 745-751 | ||
| 504 | |a Kuhn, R., Weiser, D., Fischer, H., (1959) Justus Liebigs Ann. Chem., 628, pp. 207-239 | ||
| 504 | |a Ghalambor, M.A., Levine, E.M., Heath, E.C., (1966) J. Biol. Chem., 241, pp. 3207-3215 | ||
| 504 | |a Portsmouth, D., (1968) Carbohydr. Res., 8, pp. 193-204 | ||
| 504 | |a Ramage, R., MacLeod, A.M., Rose, G.W., (1991) Tetrahedron, 47, pp. 5625-5636 | ||
| 504 | |a Plantier-Royon, R., Anker, D., Robert-Baudouy, J., (1991) J. Carbohydr. Chem., 10, pp. 239-249 | ||
| 504 | |a Charon, D., Szabo, L., (1973) J. Chem. Soc., Perkin Trans. I, pp. 1175-1179 | ||
| 504 | |a Trigalo, F., Jackymeczyk, W., Young, J.C., Szabo, L., (1975) J. Chem. Soc., Perkin Trans. I, pp. 593-598 | ||
| 504 | |a Trigalo, F., Level, M., Szabo, L., (1975) J. Chem. Soc., Perkin Trans. I, pp. 600-602 | ||
| 504 | |a Plantier-Royon, R., Cardona, F., Anker, D., Condemine, G., Nasser, W., Robert-Baudouy, J., (1991) J. Carbohydr. Chem., 10, pp. 787-811 | ||
| 504 | |a Limberg, G., Thiem, J., (1995) Carbohydr. Res., 275, pp. 107-115 | ||
| 504 | |a De Lederkremer, R.M., Varela, O., (1994) Adv. Carbohydr. Chem. Biochem., 50, pp. 125-209 | ||
| 504 | |a Di Nardo, C., Jeroncic, L.O., De Lederkremer, R.M., Varela, O., (1996) J. Org. Chem., 61, pp. 4007-4013 | ||
| 504 | |a Di Nardo, C., Varela, O., (1999) J. Org. Chem., 64, pp. 6119-6125 | ||
| 504 | |a De Lederkremer, R.M., Litter, M.I., Sala, L.F., (1974) Carbohydr. Res., 36, pp. 185-187 | ||
| 504 | |a Di Nardo, C., Varela, O., De Lederkremer, R.M., Baggio, R.F., Vega, D.R., Garland, M.T., (1995) Carbohydr. Res., 269, pp. 99-109 | ||
| 504 | |a Horton, D., Priebe, W., Sznaidman, M., (1989) Carbohydr. Res., 187, pp. 149-153 | ||
| 520 | 3 | |a Methanolysis of 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone gave methyl 3-bromo-3-deoxy-2,4,6-tri-O-benzoyl-α-D-ribo-hex-2-ulofuranosonate (3) and the anomeric mixture of the analogous 4,6-di-O-benzoyl derivative, having HO-2 free. Compound 3 was subjected to debromination with tributyltin hydride and tributyltin deuteride in the presence of 2,2'-azo-bisisobutyronitrile affording, respectively, the corresponding derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and its 3-deuterio analog. The structure of the products and intermediates was established by spectroscopic methods and chemical transformations. (C) 2000 Elsevier Science Ltd. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, TW70 | ||
| 536 | |a Detalles de la financiación: National Science and Technology Development Agency, PICT 01698 | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: Financial support from ANPCyT (National Agency for Promotion of Science and Technology, PICT 01698) and from the University of Buenos Aires (Project TW70) is gratefully acknowledged. O.V. is a Research Member of the National Research Council of República Argentina (CONICET). | ||
| 593 | |a Departamento De Química Orgánica, Facultad De Ciencias Exactas Y Naturales, Universidad De Buenos Aires, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 3-DEOXY-D-ERYTHRO-2-HEXULOSONIC ACID |
| 690 | 1 | 0 | |a 3-DEUTERIO DERIVATIVES |
| 690 | 1 | 0 | |a ALDONOLACTONES |
| 690 | 1 | 0 | |a FURANOSE DERIVATIVES OF 3-DEOXY-2-HEXULOSONIC ACID |
| 690 | 1 | 0 | |a METHANOLYSIS |
| 690 | 1 | 0 | |a 3 DEOXY DEXTRO ERYTHRO 2 HEXULOSONIC ACID DERIVATIVE |
| 690 | 1 | 0 | |a FURAN DERIVATIVE |
| 690 | 1 | 0 | |a LACTONE DERIVATIVE |
| 690 | 1 | 0 | |a METHYL 3 BROMO 3 DEOXY 2,4,6 TRI O BENZOYL ALPHA DEXTRO RIBO HEX 2 ULOFURANOSONIC ACID |
| 690 | 1 | 0 | |a METHYL 3 BROMO 3 DEOXY 4,6 DI O BENZOYL ALPHA,BETA DEXTRO RIBO HEX 2 ULOFURANOSONIC ACID |
| 690 | 1 | 0 | |a METHYL 3 DEOXY 3 DEUTERO 2,4,6 TRI O BENZOYL ALPHA DEXTRO ARABINO HEX 2 ULOFURANOSONIC ACID |
| 690 | 1 | 0 | |a METHYL 3 DEOXY 3 DEUTERO 2,4,6 TRI O BENZOYL ALPHA DEXTRO RIBO HEX 2 ULOFURANOSONIC ACID |
| 690 | 1 | 0 | |a NITRILE |
| 690 | 1 | 0 | |a TRIBUTYLTIN |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CARBOHYDRATE SYNTHESIS |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a DEBROMINATION |
| 690 | 1 | 0 | |a DEGRADATION |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a REACTION ANALYSIS |
| 690 | 1 | 0 | |a STRUCTURE ANALYSIS |
| 690 | 1 | 0 | |a BACTERIA |
| 690 | 1 | 0 | |a FURANS |
| 690 | 1 | 0 | |a GLUCONATES |
| 690 | 1 | 0 | |a KETOSES |
| 690 | 1 | 0 | |a SUGAR ACIDS |
| 690 | 1 | 0 | |a SUPPORT, NON-U.S. GOV'T |
| 700 | 1 | |a Varela, O. | |
| 773 | 0 | |d 2000 |g v. 328 |h pp. 605-610 |k n. 4 |p Carbohydr. Res. |x 00086215 |w (AR-BaUEN)CENRE-301 |t Carbohydrate Research | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0034613025&doi=10.1016%2fS0008-6215%2800%2900132-4&partnerID=40&md5=cb887ac5a9782b0507dcbfb7add2505d |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/S0008-6215(00)00132-4 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00086215_v328_n4_p605_DiNardo |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v328_n4_p605_DiNardo |y Registro en la Biblioteca Digital |
| 961 | |a paper_00086215_v328_n4_p605_DiNardo |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 63213 | ||