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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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00404020_v55_n8_p2157_Rodriguez |
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todo:paper_00404020_v55_n8_p2157_Rodriguez2023-10-03T14:50:38Z Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing Rodriguez, J.B. 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 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00404020_v55_n8_p2157_Rodriguez |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Rodriguez, J.B. Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing |
| topic_facet |
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 |
| description |
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. |
| format |
JOUR |
| author |
Rodriguez, J.B. |
| author_facet |
Rodriguez, J.B. |
| author_sort |
Rodriguez, J.B. |
| title |
Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing |
| title_short |
Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing |
| title_full |
Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing |
| title_fullStr |
Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing |
| title_full_unstemmed |
Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing |
| title_sort |
chiral 1,4-dicarbonyl-2,3-o-isopropylidene derivatives. rapid racemization on standing |
| url |
http://hdl.handle.net/20.500.12110/paper_00404020_v55_n8_p2157_Rodriguez |
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AT rodriguezjb chiral14dicarbonyl23oisopropylidenederivativesrapidracemizationonstanding |
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1807323586238611456 |