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Abstract:

In connection with the development of practical methods for the synthesis of deoxy sugars, a photoinduced electron-transfer (PET) reaction using 9-methylcarbazole (MCZ) as photosensitizer was applied to a 2-O-(3-trifluoromethyl)benzoylated derivative of d-galacturonic acid. The carboxylic group efficiently assists α-deoxygenation, the required irradiation time being significantly shorter than that in the absence of it. The photochemical reaction was also used for the deoxygenation of d-glucurono-6,3-lactone derivatives, providing in both cases the convenient routes for the synthesis of 5-deoxy-hexofuranosides and intermediate compounds for the synthesis of natural products, avoiding the use of metal hydrides. © 2007 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:5-Deoxy glycofuranosides by carboxyl group assisted photoinduced electron-transfer deoxygenation
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:Deoxy sugars; Galactofuranosides; Glucofuranosides; PET deoxygenatin; 5 deoxy glycofuranoside derivative; 5 deoxy hexofuranoside derivative; 9 methylcarbazole; carbazole derivative; carboxyl group; deoxysugar; dextro glucurono 6,3 lactone derivative; furan derivative; galacturonic acid; lactone derivative; metal; photosensitizing agent; unclassified drug; article; chemical reaction; chemical structure; deoxygenation; electron transport; irradiation; light; photochemistry; priority journal; synthesis
Año:2008
Volumen:64
Número:8
Página de inicio:1703
Página de fin:1710
DOI: http://dx.doi.org/10.1016/j.tet.2007.12.005
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
CAS:galacturonic acid, 14982-50-4, 685-73-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v64_n8_p1703_Bordoni

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Citas:

---------- APA ----------
Bordoni, A., de Lederkremer, R.M. & Marino, C. (2008) . 5-Deoxy glycofuranosides by carboxyl group assisted photoinduced electron-transfer deoxygenation. Tetrahedron, 64(8), 1703-1710.
http://dx.doi.org/10.1016/j.tet.2007.12.005
---------- CHICAGO ----------
Bordoni, A., de Lederkremer, R.M., Marino, C. "5-Deoxy glycofuranosides by carboxyl group assisted photoinduced electron-transfer deoxygenation" . Tetrahedron 64, no. 8 (2008) : 1703-1710.
http://dx.doi.org/10.1016/j.tet.2007.12.005
---------- MLA ----------
Bordoni, A., de Lederkremer, R.M., Marino, C. "5-Deoxy glycofuranosides by carboxyl group assisted photoinduced electron-transfer deoxygenation" . Tetrahedron, vol. 64, no. 8, 2008, pp. 1703-1710.
http://dx.doi.org/10.1016/j.tet.2007.12.005
---------- VANCOUVER ----------
Bordoni, A., de Lederkremer, R.M., Marino, C. 5-Deoxy glycofuranosides by carboxyl group assisted photoinduced electron-transfer deoxygenation. Tetrahedron. 2008;64(8):1703-1710.
http://dx.doi.org/10.1016/j.tet.2007.12.005