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http://hdl.handle.net/10261/18160
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Campo DC | Valor | Lengua/Idioma |
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dc.contributor.author | Abad, José Luis | - |
dc.contributor.author | Camps Díez, Francisco | - |
dc.date.accessioned | 2009-10-28T13:57:30Z | - |
dc.date.available | 2009-10-28T13:57:30Z | - |
dc.date.issued | 2004-10-08 | - |
dc.identifier.citation | Tetrahedron 60(50): 11651-11663 (2004) | en_US |
dc.identifier.issn | 0040-4020 | - |
dc.identifier.uri | http://hdl.handle.net/10261/18160 | - |
dc.description | 7 pages, 1 figure, 3 schemes.-- Printed version published Dec 6, 2004. | en_US |
dc.description.abstract | We have studied a new approach for the resolution and absolute configuration determination of the enantiomers of squalene diols as intermediate precursors in the chemical synthesis of different squalene oxides (SOs); (3R)- and (3S)-2,3-SO, (6R,7R)- and (6S,7S)-6,7-SO, and (10R,11R)- and (10S,11S)-10,11-SO. Monoderivatization of the corresponding racemic squalene diol intermediates with pure stereoisomers of (S)-(+)-methoxyphenyl acetic acid ((S)-(+)-MPA), (S)-(+)-9-anthrylmethoxyacetic acid ((S)-(+)-9-AMA) and (S)-(+)-acetoxyphenylacetic acid ((S)-(+)-APA) afforded the diastereomeric esters which could be easily separated by column flash chromatography with silica gel. In addition, the absolute configuration for these diastereoisomers of the derivatized diols was advantageously inferred from 1H NMR data according to the models depicted for these derivatizing chiral agents. In order to demonstrate the absolute configuration assignment of the different stereoisomers, (S)-(+)-AMA showed the larger Δδ by 1H NMR, however, (S)-(+)-MPA esters were much more stable derivatives. | en_US |
dc.description.sponsorship | Financial supports of this work by CICYT and FEDER (grant AGL-2001-0585) and Comissionat per a Universitats i Recerca from the Generalitat de Catalunya (grant 2001SGR-00342). | en_US |
dc.format.extent | 22195 bytes | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | en_US |
dc.publisher | Elsevier | en_US |
dc.rights | openAccess | en_US |
dc.subject | Squalene oxides | en_US |
dc.subject | Squalene diols | en_US |
dc.subject | Resolution | en_US |
dc.subject | Enantiomers | en_US |
dc.subject | Derivatization | en_US |
dc.subject | Arylacetic acids | en_US |
dc.title | Arylacetic acid derivatization of 2,3- and internal erythro-squalene diols. Separation and absolute configuration determination | en_US |
dc.type | artículo | en_US |
dc.identifier.doi | 10.1016/j.tet.2004.09.059 | - |
dc.description.peerreviewed | Peer reviewed | en_US |
dc.relation.publisherversion | http://dx.doi.org/10.1016/j.tet.2004.09.059 | en_US |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.fulltext | With Fulltext | - |
item.cerifentitytype | Publications | - |
item.openairetype | artículo | - |
item.languageiso639-1 | en | - |
item.grantfulltext | open | - |
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Abad_Jose_Luis_et_al.pdf | 348,55 kB | Adobe PDF | Visualizar/Abrir |
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