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Acetylated <jats:italic>N<\/jats:italic>\u2010benzylglucofuran\u2010 and glucopyranuronamides were synthesized in a few steps from glucofuranurono\u20106,3\u2010lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide\u2010based nucleosides by <jats:italic>N<\/jats:italic>\u2010glycosylation with silylated 2\u2010acetamido\u20106\u2010chloropurine in the presence of trimethylsilyl triflate. The triacetylated bicyclic lactone was coupled itself with the nucleobase to give bicyclic N<jats:sup>9<\/jats:sup>,N<jats:sup>7<\/jats:sup> nucleosides. Tri\u2010<jats:italic>O<\/jats:italic>\u2010acetylglucopyranurono\u20106,1\u2010lactone was used for the first time as a glycosyl donor for <jats:italic>N<\/jats:italic>\u2010glycosylation, and led to \u03b2\u2010configured <jats:italic>N<\/jats:italic><jats:sup>9<\/jats:sup>\u2010 and <jats:italic>N<\/jats:italic><jats:sup>7<\/jats:sup>\u2010linked purinylglucuronides under reaction conditions similar to those used with the 1\u2010<jats:italic>O<\/jats:italic>\u2010acetyl\u2010substituted glycosyl donors. The cholinesterase inhibitory profiles of the synthetic nucleosides bearing glucuronic acid derivatives as glycons were evaluated, and they showed moderate selective acetylcholinesterase inhibitory activities (<jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> = 14.78\u201350.53 \u03bc<jats:sc>M<\/jats:sc>). The best inhibition was shown by the furanosyl <jats:italic>N<\/jats:italic><jats:sup>9<\/jats:sup>\u2010linked uronamide\u2010based purine nucleoside.<\/jats:p>","DOI":"10.1002\/ejoc.201301913","type":"journal-article","created":{"date-parts":[[2014,3,6]],"date-time":"2014-03-06T06:29:17Z","timestamp":1394087357000},"page":"2770-2779","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["Synthesis of Purine Nucleosides from <scp>D<\/scp>\u2010Glucuronic Acid Derivatives and Evaluation of Their Cholinesterase\u2010Inhibitory Activities"],"prefix":"10.1002","volume":"2014","author":[{"given":"Nuno M.","family":"Xavier","sequence":"first","affiliation":[]},{"given":"Stefan","family":"Schwarz","sequence":"additional","affiliation":[]},{"given":"Pedro D.","family":"Vaz","sequence":"additional","affiliation":[]},{"given":"Ren\u00e9","family":"Csuk","sequence":"additional","affiliation":[]},{"given":"Am\u00e9lia P.","family":"Rauter","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2014,3,6]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF02219556"},{"key":"e_1_2_6_2_2","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)70784-2"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)90080-7"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1006\/pest.1996.0077"},{"key":"e_1_2_6_6_2","unstructured":"\u00a0"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00764a082"},{"key":"e_1_2_6_8_2","first-page":"3241","volume":"10","author":"Ichikawa Y.","year":"2004","journal-title":"Eur. 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