DC Field | Value | Language |
---|---|---|
dc.contributor.author | CHUNG, SK | - |
dc.contributor.author | RYU, YH | - |
dc.date.accessioned | 2016-03-31T14:38:11Z | - |
dc.date.available | 2016-03-31T14:38:11Z | - |
dc.date.created | 2009-02-28 | - |
dc.date.issued | 1994-05-20 | - |
dc.identifier.issn | 0008-6215 | - |
dc.identifier.other | 1994-OAK-0000008905 | - |
dc.identifier.uri | https://oasis.postech.ac.kr/handle/2014.oak/21958 | - |
dc.description.abstract | (+/-)-1,2:4,5-Di-O-isopropylidene-myo-inositol (5) and (+/-)-1,2:5,6-di-O-isopropylidene-myo-inositol (6) could be regioselectively functionalized in reactions including alkylation, acylation, and silylation at HO-3 in preference to HO-6 and HO-4, respectively, under specific conditions. The presence of intramolecular hydrogen bonding was evident in IR and H-1 NMR spectra, and the HO-3 group was identified as the hydrogen-bonding donor in 5 and 6. In their crystalline states, diol 5 prefers a chair conformation and diol 6 a twist boat (skew) conformation. Both compounds appear to have substantial populations of chair conformations in the gas and solution phases, on the basis of the MM-2 energy minimizations and comparisons of vicinal coupling constants observed in the 1H NMR spectra (in CDCl3 and Me(2)SO-d(6)) and calculated from the crystal and MM-2 conformations. It is suggested as an explanation for the observed selectivities that the kinetic acidity of the HO-3 group may be enhanced through its intramolecular hydrogen bonding with the cis-vicinal oxygen, or the nucleophilicity of the 3-alkoxide may be enhanced due to its interaction with the cis-vicinal oxygen in a manner similar to the through-space alpha-effect. | - |
dc.description.statementofresponsibility | X | - |
dc.language | English | - |
dc.publisher | ELSEVIER SCIENCE BV | - |
dc.relation.isPartOf | CARBOHYDRATE RESEARCH | - |
dc.title | REGIOSELECTIVE FUNCTIONALIZATIONS AND CONFORMATIONAL STUDIES OF DI-O-ISOPROPYLIDENE-MYO-INOSITOL DERIVATIVES | - |
dc.type | Article | - |
dc.contributor.college | 화학과 | - |
dc.identifier.doi | 10.1016/0008-6215(94)84082-2 | - |
dc.author.google | CHUNG, SK | - |
dc.author.google | RYU, YH | - |
dc.relation.volume | 258 | - |
dc.relation.startpage | 145 | - |
dc.relation.lastpage | 167 | - |
dc.contributor.id | 10200284 | - |
dc.relation.journal | CARBOHYDRATE RESEARCH | - |
dc.relation.index | SCI급, SCOPUS 등재논문 | - |
dc.relation.sci | SCI | - |
dc.collections.name | Journal Papers | - |
dc.type.rims | ART | - |
dc.identifier.bibliographicCitation | CARBOHYDRATE RESEARCH, v.258, pp.145 - 167 | - |
dc.identifier.wosid | A1994NL36300013 | - |
dc.citation.endPage | 167 | - |
dc.citation.startPage | 145 | - |
dc.citation.title | CARBOHYDRATE RESEARCH | - |
dc.citation.volume | 258 | - |
dc.contributor.affiliatedAuthor | CHUNG, SK | - |
dc.identifier.scopusid | 2-s2.0-0028436952 | - |
dc.description.journalClass | 1 | - |
dc.description.journalClass | 1 | - |
dc.description.wostc | 37 | - |
dc.type.docType | Article | - |
dc.subject.keywordPlus | NMR COUPLING-CONSTANTS | - |
dc.subject.keywordPlus | CARBOHYDRATE-CHEMISTRY | - |
dc.subject.keywordPlus | ALLYL GROUP | - |
dc.subject.keywordPlus | MYOINOSITOL PHOSPHATES | - |
dc.subject.keywordPlus | MOLECULAR MECHANICS | - |
dc.subject.keywordPlus | KARPLUS EQUATION | - |
dc.subject.keywordPlus | PROTECTION | - |
dc.relation.journalWebOfScienceCategory | Biochemistry & Molecular Biology | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Applied | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Biochemistry & Molecular Biology | - |
dc.relation.journalResearchArea | Chemistry | - |
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