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Article: Diastereospecific synthesis of 2'- or 3'-C-branched nucleosides through intramolecular free-radical capture by silicon-tethered acetylene

TitleDiastereospecific synthesis of 2'- or 3'-C-branched nucleosides through intramolecular free-radical capture by silicon-tethered acetylene
Authors
Issue Date1994
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 1994, v. 50 n. 17, p. 5255-5272 How to Cite?
AbstractThe intramolecular free-radical trapping by a silicon tethered acetylene function in a ribonucleoside 2a, 2b, 2c, 8a, 8b or 8c gave only the [3.3.0]-cis-fused Z-vinylsiloxane 3a, 3b, 3c, 9a, 9b or 9c (> 90%) in a diastereospecific manner. The temporary silicon connection from the Z-vinylsiloxane was removed by the oxidation to give the 2'- or 3'-C-branched α-keto-β-D-ribonucleoside (~ 85%), which was diastereospecifically reduced to give 1,3-syn diol (> 90%, > 97% ee) [2'- or 3'-C-branched-α-substituted R or S-hydroxymethyl-β-D-ribonucleosides 5a, 5b, 5c, 11a, 11b or 11c]. These are the first examples of highly diastereospecific synthesis of 2'- or 3'-C-branched ribonucleosides, through a 5-trig-exo radical cyclization, using the silicon-tethered approach.
Persistent Identifierhttp://hdl.handle.net/10722/179397
ISSN
2015 Impact Factor: 2.645
2015 SCImago Journal Rankings: 0.991
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorXi, Zen_US
dc.contributor.authorRong, 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. 17, p. 5255-5272en_US
dc.identifier.issn0040-4020en_US
dc.identifier.urihttp://hdl.handle.net/10722/179397-
dc.description.abstractThe intramolecular free-radical trapping by a silicon tethered acetylene function in a ribonucleoside 2a, 2b, 2c, 8a, 8b or 8c gave only the [3.3.0]-cis-fused Z-vinylsiloxane 3a, 3b, 3c, 9a, 9b or 9c (> 90%) in a diastereospecific manner. The temporary silicon connection from the Z-vinylsiloxane was removed by the oxidation to give the 2'- or 3'-C-branched α-keto-β-D-ribonucleoside (~ 85%), which was diastereospecifically reduced to give 1,3-syn diol (> 90%, > 97% ee) [2'- or 3'-C-branched-α-substituted R or S-hydroxymethyl-β-D-ribonucleosides 5a, 5b, 5c, 11a, 11b or 11c]. These are the first examples of highly diastereospecific synthesis of 2'- or 3'-C-branched ribonucleosides, through a 5-trig-exo radical cyclization, using the silicon-tethered approach.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.titleDiastereospecific synthesis of 2'- or 3'-C-branched nucleosides through intramolecular free-radical capture by silicon-tethered acetyleneen_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)90435-1en_US
dc.identifier.scopuseid_2-s2.0-0028255885en_US
dc.identifier.volume50en_US
dc.identifier.issue17en_US
dc.identifier.spage5255en_US
dc.identifier.epage5272en_US
dc.identifier.isiWOS:A1994NH15500030-
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridXi, Z=35895024600en_US
dc.identifier.scopusauthoridRong, J=7005980047en_US
dc.identifier.scopusauthoridChattopadhyaya, J=7102703837en_US

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