{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,27]],"date-time":"2026-02-27T21:59:09Z","timestamp":1772229549531,"version":"3.50.1"},"reference-count":40,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2013,2,12]],"date-time":"2013-02-12T00:00:00Z","timestamp":1360627200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2013,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A simple, regio\u2010 and stereoselective one\u2010step methodology for the mono\u2010<jats:italic>C<\/jats:italic>\u2010glycosylation of flavanone has been established. Naringenin was directly <jats:italic>C<\/jats:italic>\u2010glycosylated with <jats:sc>D<\/jats:sc>\u2010glucose by catalysis with rare\u2010earth metal triflates in acetonitrile\/water. Different reaction conditions, namely the solvent system, reaction time, energy source and catalyst were studied. Commercially available lanthanide triflates were evaluated as catalysts and praseodymium triflate proved to be the most effective for this coupling reaction. The optimized reaction conditions were applied to other monosaccharidyl donors, such as <jats:sc>D<\/jats:sc>\u2010mannose, <jats:sc>D<\/jats:sc>\u2010galactose and <jats:sc>L<\/jats:sc>\u2010rhamnose, as well as disaccharides, such as lactose and maltose, leading regio\u2010 and stereoselectively to 8\u2010<jats:italic>C<\/jats:italic>\u2010glycosyl derivatives with equatorial glycosidic bonds in yields ranging from 28 to 38\u2009%. Ultrasound irradiation was used to enhance the reaction outcome and a considerable improvement in reaction time and efficiency was achieved, allowing selective access to the target <jats:italic>C<\/jats:italic>\u2010glycosylflavanones in yields of 43\u201356\u2009%.<\/jats:p>","DOI":"10.1002\/ejoc.201201518","type":"journal-article","created":{"date-parts":[[2013,2,12]],"date-time":"2013-02-12T04:33:21Z","timestamp":1360643601000},"page":"1441-1447","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Efficient and First Regio\u2010 and Stereoselective Direct <i>C<\/i>\u2010Glycosylation of a Flavanone Catalysed by Pr(OTf)<sub>3<\/sub> Under Conventional Heating or Ultrasound Irradiation"],"prefix":"10.1002","volume":"2013","author":[{"given":"Rui G.","family":"Santos","sequence":"first","affiliation":[]},{"given":"Nuno M.","family":"Xavier","sequence":"additional","affiliation":[]},{"given":"Jo\u00e3o C.","family":"Bordado","sequence":"additional","affiliation":[]},{"given":"Am\u00e9lia P.","family":"Rauter","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2013,2,12]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1039\/b407364a"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.2174\/156802605774643015"},{"key":"e_1_2_6_3_2","first-page":"1175","volume":"2","author":"Rauter A. P.","year":"2007","journal-title":"Nat. Prod. Commun."},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1994-25393"},{"key":"e_1_2_6_5_2","volume-title":"The Chemistry of C\u2010Glycosides","author":"Levy D. E.","year":"1995"},{"key":"e_1_2_6_6_2","unstructured":"M. H. D. Postema 1995 C\u2010Glycosides Synthesis CRC Press London"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00405-0"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.5059\/yukigoseikyokaishi.56.841"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)86844-6"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)93337-4"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00825-9"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(03)01715-5"},{"key":"e_1_2_6_13_2","unstructured":"\u00a0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0158462"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol026378e"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)88479-8"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1988-27788"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.199519950362"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(97)10084-2"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0494681"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2006.03.038"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2006.03.012"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.5059\/yukigoseikyokaishi.65.175"},{"key":"e_1_2_6_24_2","first-page":"709","volume":"10","author":"Matsumoto T.","year":"1991","journal-title":"Synlett"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.2174\/138527211793797855"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2006.04.065"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/b101838h"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.02.084"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2006.02.019"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/a809914f"},{"key":"e_1_2_6_31_2","first-page":"225","author":"Ben A.","year":"2004","journal-title":"Synlett"},{"key":"e_1_2_6_32_2","first-page":"399","author":"Yamauchi T.","year":"2006","journal-title":"Synlett"},{"key":"e_1_2_6_33_2","first-page":"2818","author":"Yamauchi T.","year":"2006","journal-title":"Synthesis"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2004.07.023"},{"key":"e_1_2_6_35_2","unstructured":"\u00a0"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/cs9972600443"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.2174\/1570179054368509"},{"key":"e_1_2_6_38_2","unstructured":"\u00a0"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(01)00081-7"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo060374w"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.201201518","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.201201518","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T08:11:26Z","timestamp":1760515886000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.201201518"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,2,12]]},"references-count":40,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2013,3]]}},"alternative-id":["10.1002\/ejoc.201201518"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.201201518","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"value":"1434-193X","type":"print"},{"value":"1099-0690","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,2,12]]},"assertion":[{"value":"2012-11-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2013-02-12","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}