{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T02:06:46Z","timestamp":1791079606598,"version":"4.1.0"},"reference-count":36,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2006,11,6]],"date-time":"2006-11-06T00:00:00Z","timestamp":1162771200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2007,1,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The reaction of silylated nucleophiles with 6,1\u2010anhydroglucopyranuronic acid (glucuronic acid 6,1\u2010lactones) catalysed by tin(IV) chloride provides 1,2\u2010<jats:italic>trans<\/jats:italic> or 1,2\u2010<jats:italic>cis<\/jats:italic> (deoxy)glycosides in a manner dependent on the donor structure. The \u03b1\u2010glycoside was obtained for reactions of the donor with the 2\u2010acyl group and 2\u2010deoxydonors, whereas the 2\u2010deoxy\u20102\u2010iodo donor gave the \u03b2\u2010glycoside. Experimental evidence shows that when 1,2\u2010<jats:italic>cis<\/jats:italic>\u2010glycoside formation occurs, the anomerisation of initially formed 1,2\u2010<jats:italic>trans<\/jats:italic>\u2010glycosides catalysed by SnCl<jats:sub>4<\/jats:sub> is possible. The anomerisation of \u03b2\u2010<jats:sc>D<\/jats:sc>\u2010glucopyranosiduronic acids was found to be faster, in some cases, than anomerisation of related \u03b2\u2010<jats:sc>D<\/jats:sc>\u2010glucopyranosiduronic acid esters and \u03b2\u2010<jats:sc>D<\/jats:sc>\u2010glucopyranoside derivatives and the rates are dependent on the structure of the aglycon. Moreover, the rates of anomerisation of \u03b2\u2010<jats:sc>D<\/jats:sc>\u2010glucopyranuronic acid derivatives can be qualitatively correlated with rates of hydrolysis of \u03b2\u2010<jats:sc>D<\/jats:sc>\u2010glucopyranosiduronic acids. Mechanistic possibilities for the reactions are considered.<\/jats:p>","DOI":"10.1002\/chem.200601111","type":"journal-article","created":{"date-parts":[[2006,11,6]],"date-time":"2006-11-06T07:04:14Z","timestamp":1162796654000},"page":"902-909","source":"Crossref","is-referenced-by-count":52,"title":["Glycosidation\u2013Anomerisation Reactions of 6,1\u2010Anhydroglucopyranuronic Acid and Anomerisation of \u03b2\u2010<scp>D<\/scp>\u2010Glucopyranosiduronic Acids Promoted by SnCl<sub>4<\/sub>"],"prefix":"10.1002","volume":"13","author":[{"given":"Colin","family":"O'Brien","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Monika","family":"Pol\u00e1kov\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nigel","family":"Pitt","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manuela","family":"Tosin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paul\u2005V.","family":"Murphy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2007,1,4]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1093\/glycob\/3.2.97"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1367-5931(99)80045-3"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19860980305"},{"key":"e_1_2_6_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198602121"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2003-40349"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol026629j"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo000381z"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo049708c"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200353196"},{"key":"e_1_2_6_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200353196"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(00)80053-1"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0501994"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00199a046"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/0008-6215(94)00313-5"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja961068a"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1992-26175"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)74242-0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/P19960002873"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/b105397n"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2004.07.018"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19840960108"},{"key":"e_1_2_6_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198400711"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1993.2145"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-4731(83)90334-5"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1139\/v79-334"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(00)85697-9"},{"key":"e_1_2_6_25_2","unstructured":"\u00a0"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1139\/v65-310"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(00)81118-0"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(00)80053-1"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar050189p"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)90742-7"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.06.009"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.14-0877"},{"key":"e_1_2_6_33_2","first-page":"369","volume":"14","author":"Audichya T. 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