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Abstract:

A photoinduced electron-transfer (PET) reaction was used for the deoxygenation at C-2 of aldonolactones derivatized as 2-O-[3-(trifluoromethyl)benzoyl] or benzoyl esters. By irradiation of different d-galactono- and d-glucono-1,4-derivatives, with a 450 W lamp, using 9-methylcarbazole as photosensitizer, the corresponding 2-deoxy-d-lyxo- and 2-deoxy-d-arabino-hexono-1,4-lactones were efficiently obtained. © 2006 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Photoinduced electron-transfer α-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-d-arabino-hexono-1,4-lactone
Autor:Bordoni, A.; de Lederkremer, R.M.; Marino, C.
Filiación:CIHIDECAR (CONICET), Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon II, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:2-Deoxy-d-arabino-1,4-lactone; 2-Deoxy-d-lyxono-1,4-lactone; Aldonolactone photodeoxygenation; Deoxy sugars; Charge transfer; Irradiation; Photosensitizers; Reaction kinetics; Synthesis (chemical); 2-Deoxy-d-arabino-1,4-lactone; 2-Deoxy-d-lyxono-1,4-lactone; Aldonolactone photodeoxygenation; Deoxy sugars; Electrons; 2 deoxy 3 o [3 (trifluoromethyl)benzoyl] dextro arabinohexono 1,4 lactone; 2 deoxy 3,5,6 tri o [(3 trifluoromethyl)benzoyl] dextro arabinohexono 1,4 lactone; 2 deoxy 6 o [(3 trifluoromethyl)benzoyl] dextro arabinohexono 1,4 lactone; 2 deoxy dextro arabinohexono 1,4 lactone; 2 o [3 (trifluoromethyl)benzoyl] dextro glucono 1,4 lactone; 2 o benzoyl dextro glucono 1,4 lactone; 2,3 di o [3 (trifluoromethyl)benzoyl] dextro glucono 1,4 lactone; 2,3,5,6 tetra o [3 (trifluoromethyl)benzoyl] dextro glucono 1,4 lactone; 2,6 di o [3 (trifluoromethyl)benzoyl] dextro glucono 1,4 lactone; 3,5 di o acetyl 2 deoxy 6 o [(3 trifluoromethyl)benzoyl] dextro arabinohexono 1,4 lactone; 3,5 di o acetyl 2,6 di o [3 (trifluoromethyl)benzoyl] dextro glucono 1,4 lactone; 5,6 di o isopropylidine 2 o [3 (trifluoromethyl)benzoyl] dextro glucono 1,4 lactone; 5,6 di o isopropylidine 2,3 di o [3 (trifluoromethyl)benzoyl] dextro glucono 1,4 lactone; arabinose derivative; carbazole derivative; carbohydrate derivative; ester derivative; lactone derivative; photosensitizing agent; unclassified drug; article; chemical procedures; chemical reaction; deoxygenation; electron transport; irradiation; light; priority journal; reaction analysis; synthesis; Deoxy Sugars; Electron Transport; Glucuronates; Lactones; Magnetic Resonance Spectroscopy; Molecular Structure; Monosaccharides; Photochemistry; Sugar Acids
Año:2006
Volumen:341
Número:11
Página de inicio:1788
Página de fin:1795
DOI: http://dx.doi.org/10.1016/j.carres.2006.04.012
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:2-deoxy-D-arabino-hexono-1,4-lactone; Deoxy Sugars; galactonolactone, 2426-46-2; Glucuronates; Lactones; Monosaccharides; Sugar Acids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v341_n11_p1788_Bordoni

Referencias:

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Citas:

---------- APA ----------
Bordoni, A., de Lederkremer, R.M. & Marino, C. (2006) . Photoinduced electron-transfer α-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-d-arabino-hexono-1,4-lactone. Carbohydrate Research, 341(11), 1788-1795.
http://dx.doi.org/10.1016/j.carres.2006.04.012
---------- CHICAGO ----------
Bordoni, A., de Lederkremer, R.M., Marino, C. "Photoinduced electron-transfer α-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-d-arabino-hexono-1,4-lactone" . Carbohydrate Research 341, no. 11 (2006) : 1788-1795.
http://dx.doi.org/10.1016/j.carres.2006.04.012
---------- MLA ----------
Bordoni, A., de Lederkremer, R.M., Marino, C. "Photoinduced electron-transfer α-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-d-arabino-hexono-1,4-lactone" . Carbohydrate Research, vol. 341, no. 11, 2006, pp. 1788-1795.
http://dx.doi.org/10.1016/j.carres.2006.04.012
---------- VANCOUVER ----------
Bordoni, A., de Lederkremer, R.M., Marino, C. Photoinduced electron-transfer α-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-d-arabino-hexono-1,4-lactone. Carbohydr. Res. 2006;341(11):1788-1795.
http://dx.doi.org/10.1016/j.carres.2006.04.012