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Abstract:

1,4-Dicarbonyl-2,3-chiral derivatives are useful synthetic precursors for the preparation of carbocyclic rings but, in many cases, losses of optical purity have been reported. 1-Deoxy-3,4-O-isopropylidene-6-O-trityl- D-erythro-hexo-2,5-diulose and 1-deoxy-3,4-O-isopropylidene-6-O-(tert- butyldiphenylsilyl)-D-erythro-hexo-2,5-diulose were synthesized from D- ribono-1,4-lactone. These compounds were selected to study the epimerizability of 2,3-O-isopropylidene-1,4-dicarbonyl derivatives. It was found that both compounds smoothly epimerize and partially racemize on standing.

Registro:

Documento: Artículo
Título:Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing
Autor:Rodriguez, J.B.
Filiación:Departamento de Quimica Organica, Facultad de Cie. Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, RA-1428 Buenos Aires, Argentina
Palabras clave:Carbohydrates; Epimerization; Nucleosides; Racemization; 1 deoxy 3,4 o isopropylidene 6 o (tert butyldiphenylsilyl)erythrohexo 2,5 diulose; 1 deoxy 3,4 o isopropylidene 6 o tritylerythrohexo 2,5 diulose; 1,4 dicarbonyl 2,3 o isopropylidene derivative; carbonyl derivative; lactone derivative; ribono 1,4 lactone; unclassified drug; article; chirality; drug synthesis; priority journal; racemic mixture; standing
Año:1999
Volumen:55
Número:8
Página de inicio:2157
Página de fin:2170
DOI: http://dx.doi.org/10.1016/S0040-4020(99)00007-1
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v55_n8_p2157_Rodriguez

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Citas:

---------- APA ----------
(1999) . Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing. Tetrahedron, 55(8), 2157-2170.
http://dx.doi.org/10.1016/S0040-4020(99)00007-1
---------- CHICAGO ----------
Rodriguez, J.B. "Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing" . Tetrahedron 55, no. 8 (1999) : 2157-2170.
http://dx.doi.org/10.1016/S0040-4020(99)00007-1
---------- MLA ----------
Rodriguez, J.B. "Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing" . Tetrahedron, vol. 55, no. 8, 1999, pp. 2157-2170.
http://dx.doi.org/10.1016/S0040-4020(99)00007-1
---------- VANCOUVER ----------
Rodriguez, J.B. Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing. Tetrahedron. 1999;55(8):2157-2170.
http://dx.doi.org/10.1016/S0040-4020(99)00007-1