{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T09:05:55Z","timestamp":1791018355666,"version":"4.1.0"},"reference-count":48,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,8,21]],"date-time":"2026-08-21T00:00:00Z","timestamp":1787270400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,8,21]],"date-time":"2026-08-21T00:00:00Z","timestamp":1787270400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    A repertoire of phosphonomethyl (thio)phosphonamidite reagents has been developed to enable the controlled synthesis of phosphonylmethyl phosphono(di)thioate analogues of intrinsically labile pyrophosphates. Selective amidophosphonitylation of an alcohol or thiol of choice with a phosphonomethyl phosphonbisamidite allows access to four (thio)phosphonamidite reagents bearing three orthogonal protecting groups that can be chemoselectively addressed. These reagents were isolated in homogeneous form in yields up to 95% and applied in a sequence involving azole\u2010mediated phosphonamidite coupling with an alcohol and successive in situ sulfurization of the P\n                    <jats:sup>III<\/jats:sup>\n                    \u2010P\n                    <jats:sup>V<\/jats:sup>\n                    intermediate, which affords protected phosphonylmethyl phosphono(di)thioate tetraesters. The coupling and sulfurization steps were monitored with\n                    <jats:sup>31<\/jats:sup>\n                    P\u2010NMR, revealing the nature of the key intermediates and corroborating the high efficiency of the coupling and sulfurization reactions. Immediate global deprotection or subsequent site\u2010selective deprotection of the terminal phosphonate followed by a phosphonodiester condensation furnishes unprecedented phosphonylmethyl phosphono(di)thioate mono\u2010 and nonsymmetrical diesters, respectively. Using this method, we have assembled four nucleoside diphosphate analogs as well as a set of eight stable CDP\u2010glycerol and CDP\u2010ribitol mimics, all in multimilligram amounts.\n                  <\/jats:p>","DOI":"10.1002\/chem.71563","type":"journal-article","created":{"date-parts":[[2026,8,21]],"date-time":"2026-08-21T13:35:33Z","timestamp":1787319333000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Phosphonomethyl (Thio)Phosphonamidite Reagents for the Construction of Phosphonylmethyl Phosphono(Di)Thioate Mono\u2010 and Diesters"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0009-0005-9542-7625","authenticated-orcid":false,"given":"Pascal","family":"Bali\u0107","sequence":"first","affiliation":[{"name":"Leiden Institute of Chemistry Leiden University  Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9243-8477","authenticated-orcid":false,"given":"Roy","family":"Steneker","sequence":"additional","affiliation":[{"name":"Leiden Institute of Chemistry Leiden University  Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9577-2123","authenticated-orcid":false,"given":"Gijsbert A. van der","family":"Marel","sequence":"additional","affiliation":[{"name":"Leiden Institute of Chemistry Leiden University  Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3531-2138","authenticated-orcid":false,"given":"Jeroen D. C.","family":"Cod\u00e9e","sequence":"additional","affiliation":[{"name":"Leiden Institute of Chemistry Leiden University  Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6978-7425","authenticated-orcid":false,"given":"Dmitri V.","family":"Filippov","sequence":"additional","affiliation":[{"name":"Leiden Institute of Chemistry Leiden University  Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,8,21]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.3390\/sym13050889"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41580\u2010020\u201000313\u2010x"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1042\/BJ20130118"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2020.10.007"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00537"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jbc.2022.102171"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1055\/s\u20100036\u20101591922"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25225268"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201601754"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/ddr.21877"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschembio.5b00972"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2014.05.001"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo061087v"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bone.2021.116289"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202004590"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611878"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198304233"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021\u20109258(20)65184\u20105"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschembio.0c00864"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1089\/nat.2014.0506"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b01906"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic400878k"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c05655"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00270F"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01028a005"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo016105h"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB02007C"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)99887\u20103"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1984.1229"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/12.10.4051"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/14.18.7391"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00212a003"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.43\u20100896"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104020(97)00924\u20101"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo960274y"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol801608j"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00017a033"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00159a059"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201605056"},{"issue":"5","key":"e_1_2_7_41_1","doi-asserted-by":"crossref","first-page":"1011","DOI":"10.1080\/07328318908054265","article-title":"Synthesis of Oligodeoxynucleotides Containing Specific Methylphosphonothioate and Dithioate Moieties","volume":"8","author":"Brill W. 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