{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2023,11,13]],"date-time":"2023-11-13T21:10:06Z","timestamp":1699909806452},"reference-count":36,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2008,10,20]],"date-time":"2008-10-20T00:00:00Z","timestamp":1224460800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2009,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:italic>R<\/jats:italic><jats:sub>P<\/jats:sub>\u2010 and <jats:italic>S<\/jats:italic><jats:sub>P<\/jats:sub>\u2010 diastereomers of 5\u2032\u2010dimethoxytrityl\u2010thymidine\u20103\u2032\u2010<jats:italic>O<\/jats:italic>\u2010[<jats:italic>O<\/jats:italic>\u2010(2\u2010cyanoethyl)\u2010<jats:italic>N,N<\/jats:italic>\u2010diisopropyl]\u2010phosphoramidite (T\u2010CED) were separated by silica gel chromatography. Oxidation of both isomers with H<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>, elemental sulfur and selenium, respectively, resulted in the corresponding oxidized analogues in nearly quantitative yields. All reactions were found to proceed with retention of <jats:italic>P<\/jats:italic>\u2010configuration. This was confirmed by thorough NMR analysis which, in addition, aimed to study the spectral properties of the diastereomers with special respect to differences in the heteroatom effect of the O, S and Se atoms, double\u2010bonded to the phosphorus, on the vicinal carbon\u2013phosphorus couplings. It was found that the changes in the \u0394<jats:italic>J<\/jats:italic> (=<jats:sup>3<\/jats:sup><jats:italic>J<\/jats:italic>(P,C4\u2032) \u2212 <jats:sup>3<\/jats:sup><jats:italic>J<\/jats:italic>(P,C2\u2032)) values were basically induced by the electronegativity of the heteroatoms, rather than differences in the rotational preferences about the C3\u2032\u2010O3\u2032 bond. The impact of the benzene solvent on the above couplings is also discussed. The effect of these heteroatoms on the chromatographic (normal and reverse phase HPLC) behavior of the compounds was also investigated and the reverse phase HPLC profiles showed an unambiguous correlation between the electronegativity of the heteroatoms and the chromatographic mobility of the analogues. Chirality, 2009. \u00a9 2008 Wiley\u2010Liss, Inc.<\/jats:p>","DOI":"10.1002\/chir.20653","type":"journal-article","created":{"date-parts":[[2008,10,20]],"date-time":"2008-10-20T17:34:08Z","timestamp":1224524048000},"page":"663-673","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and structural study of variously oxidized diastereomeric 5\u2032\u2010dimethoxytrityl\u2010thymidine\u20103\u2032\u2010<i>O<\/i>\u2010[<i>O<\/i>\u2010(2\u2010cyanoethyl)\u2010<i>N,N<\/i>\u2010diisopropyl]\u2010phosphoramidite derivatives. Comparison of the effects of the P\uf8feO, P\uf8feS, and P\uf8feSe functions on the NMR spectral and chromatographic properties"],"prefix":"10.1002","volume":"21","author":[{"given":"Eszter","family":"G\u00e1cs\u2010Baitz","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ferenc","family":"Sipos","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Orsolya","family":"Egyed","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gyula","family":"S\u00e1gi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2008,10,20]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(95)00313-W"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/0957-4166(96)00303-5"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1080\/07328319808004319"},{"key":"e_1_2_1_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/1520-636X(2000)12:9<675::AID-CHIR6>3.0.CO;2-L"},{"key":"e_1_2_1_6_2","doi-asserted-by":"publisher","DOI":"10.1080\/15257770008033031"},{"key":"e_1_2_1_7_2","doi-asserted-by":"publisher","DOI":"10.1081\/NCN-100105899"},{"key":"e_1_2_1_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.10144"},{"key":"e_1_2_1_9_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00216-003-2486-9"},{"key":"e_1_2_1_10_2","doi-asserted-by":"publisher","DOI":"10.1081\/NCN-59691"},{"key":"e_1_2_1_11_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/13.3.927"},{"key":"e_1_2_1_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00012a017"},{"key":"e_1_2_1_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39900001154"},{"key":"e_1_2_1_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol000364w"},{"key":"e_1_2_1_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(01)80524-2"},{"key":"e_1_2_1_16_2","doi-asserted-by":"publisher","DOI":"10.1080\/07328319908044872"},{"key":"e_1_2_1_17_2","unstructured":"ScozzariAN KrotzAH(Isis Pharmaceuticals Inc. 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