Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent
Identifieur interne : 001599 ( Main/Exploration ); précédent : 001598; suivant : 001600Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent
Auteurs : Pelayo Camps [Belgique, Espagne] ; Ta Nia Go Mez [Belgique, Espagne] ; Diego Mun Oz-Torrero [Belgique, Espagne] ; Jordi Rull [Belgique, Espagne] ; Laura Sa Nchez [Belgique, Espagne] ; Francesca Boschi [Belgique, Espagne] ; Mauro Comes-Franchini [Belgique] ; Alfredo Ricci [Belgique] ; Teresa Calvet [Belgique, Espagne] ; Merce Font-Bardia [Belgique, Espagne] ; Erik De Clercq [Belgique] ; Lieve Naesens [Belgique]Source :
- The Journal of Organic Chemistry [ 0022-3263 ] ; 2008.
Abstract
A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2,3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.
Url:
DOI: 10.1021/jo800769m
Affiliations:
- Belgique, Espagne
- Catalogne, Province du Brabant flamand, Région flamande
- Barcelone, Louvain
- Katholieke Universiteit Leuven, Université de Barcelone
Links toward previous steps (curation, corpus...)
- to stream Istex, to step Corpus: 000651
- to stream Istex, to step Curation: 000618
- to stream Istex, to step Checkpoint: 000149
- to stream Main, to step Merge: 001603
- to stream Main, to step Curation: 001599
Le document en format XML
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Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="4"><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName><orgName type="university">Université de Barcelone</orgName></affiliation></author><author><name sortKey="Go Mez, Ta Nia" sort="Go Mez, Ta Nia" uniqKey="Go Mez T" first="Ta Nia" last="Go Mez">Ta Nia Go Mez</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="4"><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName><orgName type="university">Université de Barcelone</orgName></affiliation></author><author><name sortKey="Mun Oz Torrero, Diego" sort="Mun Oz Torrero, Diego" uniqKey="Mun Oz Torrero D" first="Diego" last="Mun Oz-Torrero">Diego Mun Oz-Torrero</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="4"><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName><orgName type="university">Université de Barcelone</orgName></affiliation></author><author><name sortKey="Rull, Jordi" sort="Rull, Jordi" uniqKey="Rull J" first="Jordi" last="Rull">Jordi Rull</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="4"><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName><orgName type="university">Université de Barcelone</orgName></affiliation></author><author><name sortKey="Sa Nchez, Laura" sort="Sa Nchez, Laura" uniqKey="Sa Nchez L" first="Laura" last="Sa Nchez">Laura Sa Nchez</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="4"><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName><orgName type="university">Université de Barcelone</orgName></affiliation></author><author><name sortKey="Boschi, Francesca" sort="Boschi, Francesca" uniqKey="Boschi F" first="Francesca" last="Boschi">Francesca Boschi</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="4"><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName><orgName type="university">Université de Barcelone</orgName></affiliation></author><author><name sortKey="Comes Franchini, Mauro" sort="Comes Franchini, Mauro" uniqKey="Comes Franchini M" first="Mauro" last="Comes-Franchini">Mauro Comes-Franchini</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Ricci, Alfredo" sort="Ricci, Alfredo" uniqKey="Ricci A" first="Alfredo" last="Ricci">Alfredo Ricci</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Calvet, Teresa" sort="Calvet, Teresa" uniqKey="Calvet T" first="Teresa" last="Calvet">Teresa Calvet</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="4"><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName><orgName type="university">Université de Barcelone</orgName></affiliation></author><author><name sortKey="Font Bardia, Merce" sort="Font Bardia, Merce" uniqKey="Font Bardia M" first="Merce" last="Font-Bardia">Merce Font-Bardia</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="4"><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName><orgName type="university">Université de Barcelone</orgName></affiliation></author><author><name sortKey="Clercq, Erik De" sort="Clercq, Erik De" uniqKey="Clercq E" first="Erik De" last="Clercq">Erik De Clercq</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="4"><country>Belgique</country><placeName><settlement type="city">Louvain</settlement><region>Région flamande</region><region type="district" nuts="2">Province du Brabant flamand</region></placeName><orgName type="university">Katholieke Universiteit Leuven</orgName></affiliation></author><author><name sortKey="Naesens, Lieve" sort="Naesens, Lieve" uniqKey="Naesens L" first="Lieve" last="Naesens">Lieve Naesens</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain, Department of Organic Chemistry “A. Mangini”, University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Serveis Científico-Tècnics, Universitat de Barcelona, Av. Martí Franquès s/n, E-08028 Barcelona, Spain, and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université de Barcelone</orgName><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="4"><country>Belgique</country><placeName><settlement type="city">Louvain</settlement><region>Région flamande</region><region type="district" nuts="2">Province du Brabant flamand</region></placeName><orgName type="university">Katholieke Universiteit Leuven</orgName></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">The Journal of Organic Chemistry</title><title level="j" type="abbrev">J. Org. Chem.</title><idno type="ISSN">0022-3263</idno><idno type="eISSN">1520-6904</idno><imprint><publisher>American Chemical Society</publisher><date type="e-published" when="2008-07-29">2008</date><date when="2008-09-05">2008</date><biblScope unit="vol">73</biblScope><biblScope unit="issue">17</biblScope><biblScope unit="page" from="6657">6657</biblScope><biblScope unit="page" to="6665">6665</biblScope></imprint><idno type="ISSN">0022-3263</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0022-3263</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract">A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2,3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.</div></front></TEI><affiliations><list><country><li>Belgique</li><li>Espagne</li></country><region><li>Catalogne</li><li>Province du Brabant flamand</li><li>Région flamande</li></region><settlement><li>Barcelone</li><li>Louvain</li></settlement><orgName><li>Katholieke Universiteit Leuven</li><li>Université de Barcelone</li></orgName></list><tree><country name="Belgique"><region name="Catalogne"><name sortKey="Camps, Pelayo" sort="Camps, Pelayo" uniqKey="Camps P" first="Pelayo" last="Camps">Pelayo Camps</name></region><name sortKey="Boschi, Francesca" sort="Boschi, Francesca" uniqKey="Boschi F" first="Francesca" last="Boschi">Francesca Boschi</name><name sortKey="Calvet, Teresa" sort="Calvet, Teresa" uniqKey="Calvet T" first="Teresa" last="Calvet">Teresa Calvet</name><name sortKey="Clercq, Erik De" sort="Clercq, Erik De" uniqKey="Clercq E" first="Erik De" last="Clercq">Erik De Clercq</name><name sortKey="Clercq, Erik De" sort="Clercq, Erik De" uniqKey="Clercq E" first="Erik De" last="Clercq">Erik De Clercq</name><name sortKey="Comes Franchini, Mauro" sort="Comes Franchini, Mauro" uniqKey="Comes Franchini M" first="Mauro" last="Comes-Franchini">Mauro Comes-Franchini</name><name sortKey="Font Bardia, Merce" sort="Font Bardia, Merce" uniqKey="Font Bardia M" first="Merce" last="Font-Bardia">Merce Font-Bardia</name><name sortKey="Go Mez, Ta Nia" sort="Go Mez, Ta Nia" uniqKey="Go Mez T" first="Ta Nia" last="Go Mez">Ta Nia Go Mez</name><name sortKey="Mun Oz Torrero, Diego" sort="Mun Oz Torrero, Diego" uniqKey="Mun Oz Torrero D" first="Diego" last="Mun Oz-Torrero">Diego Mun Oz-Torrero</name><name sortKey="Naesens, Lieve" sort="Naesens, Lieve" uniqKey="Naesens L" first="Lieve" last="Naesens">Lieve Naesens</name><name sortKey="Naesens, Lieve" sort="Naesens, Lieve" uniqKey="Naesens L" first="Lieve" last="Naesens">Lieve Naesens</name><name sortKey="Ricci, Alfredo" sort="Ricci, Alfredo" uniqKey="Ricci A" first="Alfredo" last="Ricci">Alfredo Ricci</name><name sortKey="Rull, Jordi" sort="Rull, Jordi" uniqKey="Rull J" first="Jordi" last="Rull">Jordi Rull</name><name sortKey="Sa Nchez, Laura" sort="Sa Nchez, Laura" uniqKey="Sa Nchez L" first="Laura" last="Sa Nchez">Laura Sa Nchez</name></country><country name="Espagne"><region name="Catalogne"><name sortKey="Camps, Pelayo" sort="Camps, Pelayo" uniqKey="Camps P" first="Pelayo" last="Camps">Pelayo Camps</name></region><name sortKey="Boschi, Francesca" sort="Boschi, Francesca" uniqKey="Boschi F" first="Francesca" last="Boschi">Francesca Boschi</name><name sortKey="Calvet, Teresa" sort="Calvet, Teresa" uniqKey="Calvet T" first="Teresa" last="Calvet">Teresa Calvet</name><name sortKey="Font Bardia, Merce" sort="Font Bardia, Merce" uniqKey="Font Bardia M" first="Merce" last="Font-Bardia">Merce Font-Bardia</name><name sortKey="Go Mez, Ta Nia" sort="Go Mez, Ta Nia" uniqKey="Go Mez T" first="Ta Nia" last="Go Mez">Ta Nia Go Mez</name><name sortKey="Mun Oz Torrero, Diego" sort="Mun Oz Torrero, Diego" uniqKey="Mun Oz Torrero D" first="Diego" last="Mun Oz-Torrero">Diego Mun Oz-Torrero</name><name sortKey="Rull, Jordi" sort="Rull, Jordi" uniqKey="Rull J" first="Jordi" last="Rull">Jordi Rull</name><name sortKey="Sa Nchez, Laura" sort="Sa Nchez, Laura" uniqKey="Sa Nchez L" first="Laura" last="Sa Nchez">Laura Sa Nchez</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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|texte= Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent
}}
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