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Article: The synthesis and conformation of 2'- and 3'-hypermodified tricyclic nucleosides and their use in the synthesis of novel 2'- or 3'-isomeric 4(7)- substituted isoxazolidine-nucleosides

TitleThe synthesis and conformation of 2'- and 3'-hypermodified tricyclic nucleosides and their use in the synthesis of novel 2'- or 3'-isomeric 4(7)- substituted isoxazolidine-nucleosides
Authors
Issue Date1994
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 1994, v. 50 n. 16, p. 4921-4936 How to Cite?
AbstractIntramolecular 1,3-dipolar cycloaddition reactions of a number of C- alkenyl nitrones of nucleoside derivatives 7, 9, 19 and 28 afforded 2'- and 3'-hypermodified tricyclic nucleoside derivatives 10 (56%), 11 (43%), 20 (91%) and 29 (15%), respectively. The solution structures of these tricyclic nucleoside derivatives have been investigated using the 3J(HH) (1H at 500 MHz) and the NMR-derived torsion angle constrained energy minimizations with the aid of MacroModel's AMBER force field. Subsequent Tamao oxidation of the hypermodified nucleoside derivatives 20 and 29 gave spiro-4(7)-substituted isoxazolidine-nucleoside derivatives 21 and 30, respectively.
Persistent Identifierhttp://hdl.handle.net/10722/179396
ISSN
2015 Impact Factor: 2.645
2015 SCImago Journal Rankings: 0.991
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorRong, Jen_US
dc.contributor.authorRoselt, Pen_US
dc.contributor.authorPlavec, Jen_US
dc.contributor.authorChattopadhyaya, Jen_US
dc.date.accessioned2012-12-19T09:56:09Z-
dc.date.available2012-12-19T09:56:09Z-
dc.date.issued1994en_US
dc.identifier.citationTetrahedron, 1994, v. 50 n. 16, p. 4921-4936en_US
dc.identifier.issn0040-4020en_US
dc.identifier.urihttp://hdl.handle.net/10722/179396-
dc.description.abstractIntramolecular 1,3-dipolar cycloaddition reactions of a number of C- alkenyl nitrones of nucleoside derivatives 7, 9, 19 and 28 afforded 2'- and 3'-hypermodified tricyclic nucleoside derivatives 10 (56%), 11 (43%), 20 (91%) and 29 (15%), respectively. The solution structures of these tricyclic nucleoside derivatives have been investigated using the 3J(HH) (1H at 500 MHz) and the NMR-derived torsion angle constrained energy minimizations with the aid of MacroModel's AMBER force field. Subsequent Tamao oxidation of the hypermodified nucleoside derivatives 20 and 29 gave spiro-4(7)-substituted isoxazolidine-nucleoside derivatives 21 and 30, respectively.en_US
dc.languageengen_US
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/teten_US
dc.relation.ispartofTetrahedronen_US
dc.titleThe synthesis and conformation of 2'- and 3'-hypermodified tricyclic nucleosides and their use in the synthesis of novel 2'- or 3'-isomeric 4(7)- substituted isoxazolidine-nucleosidesen_US
dc.typeArticleen_US
dc.identifier.emailRong, J: jrong@hku.hken_US
dc.identifier.authorityRong, J=rp00515en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1016/S0040-4020(01)85027-4en_US
dc.identifier.scopuseid_2-s2.0-0028238039en_US
dc.identifier.volume50en_US
dc.identifier.issue16en_US
dc.identifier.spage4921en_US
dc.identifier.epage4936en_US
dc.identifier.isiWOS:A1994NF66800026-
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridRong, J=7005980047en_US
dc.identifier.scopusauthoridRoselt, P=11241438200en_US
dc.identifier.scopusauthoridPlavec, J=7003379618en_US
dc.identifier.scopusauthoridChattopadhyaya, J=7102703837en_US

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