{"?xml":{"@version":"1.0"},"edm:RDF":{"@xmlns:dc":"http://purl.org/dc/elements/1.1/","@xmlns:edm":"http://www.europeana.eu/schemas/edm/","@xmlns:wgs84_pos":"http://www.w3.org/2003/01/geo/wgs84_pos","@xmlns:foaf":"http://xmlns.com/foaf/0.1/","@xmlns:rdaGr2":"http://rdvocab.info/ElementsGr2","@xmlns:oai":"http://www.openarchives.org/OAI/2.0/","@xmlns:owl":"http://www.w3.org/2002/07/owl#","@xmlns:rdf":"http://www.w3.org/1999/02/22-rdf-syntax-ns#","@xmlns:ore":"http://www.openarchives.org/ore/terms/","@xmlns:skos":"http://www.w3.org/2004/02/skos/core#","@xmlns:dcterms":"http://purl.org/dc/terms/","edm:WebResource":[{"@rdf:about":"http://www.dlib.si/stream/URN:NBN:SI:doc-H645T7JP/577a5243-8351-463b-8f85-4ec07ed6b42b/PDF","dcterms:extent":"206 KB"},{"@rdf:about":"http://www.dlib.si/stream/URN:NBN:SI:doc-H645T7JP/a4e22763-90c8-4864-aad8-4f05e0241642/TEXT","dcterms:extent":"29 KB"}],"edm:ProvidedCHO":{"@rdf:about":"URN:NBN:SI:doc-H645T7JP","dcterms:issued":"2026","dc:creator":["Gobec, Stanislav","Hrast Rambaher, Martina","Kavaš, Vid","Lukić, David"],"dc:contributor":["Gobec, Stanislav","Hrast Rambaher, Martina"],"dc:format":[{"@xml:lang":"sl","#text":"številka:3"},{"@xml:lang":"sl","#text":"letnik:73"},{"@xml:lang":"sl","#text":"str. 554-559"}],"dc:identifier":["DOI:10.17344/acsi.2026.9857","ISSN:1580-3155","COBISSID_HOST:288035075","URN:URN:NBN:SI:doc-H645T7JP"],"dc:language":"en","dc:publisher":{"@xml:lang":"sl","#text":"Slovensko kemijsko društvo"},"dc:source":{"@xml:lang":"sl","#text":"Acta chimica slovenica"},"dc:subject":[{"@xml:lang":"sl","#text":"Farmacevtska kemija"},{"@xml:lang":"sl","#text":"monociklični ß-laktami"},{"@xml:lang":"en","#text":"monocyclic ß-lactams"},{"@xml:lang":"sl","#text":"odstranjevanje zaščite s TBDMS"},{"@xml:lang":"sl","#text":"presejanje pogojev odstranjevanja zaščite"},{"@xml:lang":"en","#text":"screening of deprotection conditions"},{"@xml:lang":"en","#text":"TBDMS deprotection"}],"dc:title":{"@xml:lang":"sl","#text":"Screening of deprotection conditions of TBDMS protecting group on ß-lactams|"},"dc:description":[{"@xml:lang":"sl","#text":"Monocyclic ß-lactams are valuable scaffolds for the development of novel antibacterial agents, and synthetic flexibility at the C3 position of the ß-lactam ring is of particular interest. In this study, we evaluated multiple procedures for the deprotection of the tertbutyldimethylsilyl (TBDMS) group in model azetidinone derivatives to enable early-stage functionalization of the C3 hydroxyl group. Given the sensitivity of the strained ß-lactam ring and the presence of additional labile functionalities, careful selection of reaction conditions was required. Two optimized deprotection protocols were identified that successfully afforded the corresponding free alcohols, even in the presence of an acid- and base-sensitive dithiocarbamate moiety. In contrast, several literature-reported procedures proved ineffective under the tested conditions. Although the isolated yields were modest, the results demonstrate the feasibility of selective TBDMS removal in structurally complex monocyclic ß-lactam systems. These findings establish a foundation for further optimization and provide a basis for expanding C3 functionalization strategies in the synthesis of novel ß-lactam derivatives"},{"@xml:lang":"sl","#text":"Monociklični ß-laktami so pomembni za razvoj novih protibakterijskih učinkovin, pri čemer je posebej zanimiva sintezna prilagodljivost na položaju C3 ß-laktamskega obroča. V prispevku smo opisali več postopkov za odstranjevanje terc-butil dimetilsilil (TBDMS) zaščitne skupine v modelnih azetidinonskih derivatih, ki omogočijo funkcionalizacijo hidroksilne skupine C3 v zgodnjih fazah sinteze. Zaradi občutljivosti ß-laktamskega obroča in prisotnost dodatnih občutljivih funkcionalnih skupin, smo morali reakcijske pogoje skrbno nadzorovati. Opisali smo dva optimizirana protokola za odstranjevanje zaščitnih skupin, ki sta privedla do ustreznih prostih alkoholov, celo v prisotnosti na kisline in baze občutljive ditiokarbamatne funkcionalne skupine. Več metod, navedenih v literaturi, se je pri testiranih pogojih izkazalo za neučinkovite. Čeprav so bili izkoristki (11–15 %) skromni, rezultati kažejo na izvedljivost selektivnega odstranjevanja TBDMS v strukturno kompleksnih monocikličnih ß-laktamih. Opisane ugotovitve postavljajo temelje za nadaljnjo optimizacijo in funkcionalizacijo položaja C3 pri sintezi novih ß-laktamov"}],"edm:type":"TEXT","dc:type":[{"@xml:lang":"sl","#text":"znanstveno časopisje"},{"@xml:lang":"en","#text":"journals"},{"@rdf:resource":"http://www.wikidata.org/entity/Q361785"}]},"ore:Aggregation":{"@rdf:about":"http://www.dlib.si/?URN=URN:NBN:SI:doc-H645T7JP","edm:aggregatedCHO":{"@rdf:resource":"URN:NBN:SI:doc-H645T7JP"},"edm:isShownBy":{"@rdf:resource":"http://www.dlib.si/stream/URN:NBN:SI:doc-H645T7JP/577a5243-8351-463b-8f85-4ec07ed6b42b/PDF"},"edm:rights":{"@rdf:resource":"http://creativecommons.org/licenses/by/4.0/"},"edm:provider":"Slovenian National E-content Aggregator","edm:intermediateProvider":{"@xml:lang":"en","#text":"National and University Library of Slovenia"},"edm:dataProvider":{"@xml:lang":"sl","#text":"Slovensko kemijsko društvo"},"edm:object":{"@rdf:resource":"http://www.dlib.si/streamdb/URN:NBN:SI:doc-H645T7JP/maxi/edm"},"edm:isShownAt":{"@rdf:resource":"http://www.dlib.si/details/URN:NBN:SI:doc-H645T7JP"}}}}