Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing

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- butyldipheny...

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Detalles Bibliográficos
Autor principal: Rodriguez, J.B.
Formato: JOUR
Materias:
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
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00404020_v55_n8_p2157_Rodriguez
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario: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.

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