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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs
Autor:Di Nardo, C.; Varela, O.
Filiación:Departamento De Química Orgánica, Facultad De Ciencias Exactas Y Naturales, Universidad De Buenos Aires, 1428 Buenos Aires, Argentina
Palabras clave:3-Deoxy-D-erythro-2-hexulosonic acid; 3-Deuterio derivatives; Aldonolactones; Furanose derivatives of 3-deoxy-2-hexulosonic acid; Methanolysis; 3 deoxy dextro erythro 2 hexulosonic acid derivative; furan derivative; lactone derivative; methyl 3 bromo 3 deoxy 2,4,6 tri o benzoyl alpha dextro ribo hex 2 ulofuranosonic acid; methyl 3 bromo 3 deoxy 4,6 di o benzoyl alpha,beta dextro ribo hex 2 ulofuranosonic acid; methyl 3 deoxy 3 deutero 2,4,6 tri o benzoyl alpha dextro arabino hex 2 ulofuranosonic acid; methyl 3 deoxy 3 deutero 2,4,6 tri o benzoyl alpha dextro ribo hex 2 ulofuranosonic acid; nitrile; tributyltin; unclassified drug; article; carbohydrate synthesis; chemical structure; debromination; degradation; priority journal; reaction analysis; structure analysis; Bacteria; Furans; Gluconates; Ketoses; Sugar Acids; Support, Non-U.S. Gov't
Año:2000
Volumen:328
Número:4
Página de inicio:605
Página de fin:610
DOI: http://dx.doi.org/10.1016/S0008-6215(00)00132-4
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:3-deoxyhexulose, 6196-57-2; Furans; galactonic acid, 13382-27-9; Gluconates; Ketoses; Sugar Acids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v328_n4_p605_DiNardo

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Citas:

---------- APA ----------
Di Nardo, C. & Varela, O. (2000) . Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs. Carbohydrate Research, 328(4), 605-610.
http://dx.doi.org/10.1016/S0008-6215(00)00132-4
---------- CHICAGO ----------
Di Nardo, C., Varela, O. "Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs" . Carbohydrate Research 328, no. 4 (2000) : 605-610.
http://dx.doi.org/10.1016/S0008-6215(00)00132-4
---------- MLA ----------
Di Nardo, C., Varela, O. "Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs" . Carbohydrate Research, vol. 328, no. 4, 2000, pp. 605-610.
http://dx.doi.org/10.1016/S0008-6215(00)00132-4
---------- VANCOUVER ----------
Di Nardo, C., Varela, O. Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs. Carbohydr. Res. 2000;328(4):605-610.
http://dx.doi.org/10.1016/S0008-6215(00)00132-4