{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,8,11]],"date-time":"2024-08-11T05:11:59Z","timestamp":1723353119691},"reference-count":22,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2014,3,26]],"date-time":"2014-03-26T00:00:00Z","timestamp":1395792000000},"content-version":"vor","delay-in-days":25,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["CP Nucleic Acid Chemistry"],"published-print":{"date-parts":[[2014,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Nucleoside phosphonate analogs are an important class of antiviral drugs for the treatment of HIV and HBV. The most recent nucleoside phosphonate to progress to clinical development is GS\u20109131, a cyclic nucleoside phosphonate (CNP). This unit contains procedures for the synthesis of the parent CNP 2\u2032\u2010Fd4AP (GS\u20109148) and selected monoamidate and bisamidate prodrugs, including the monoamidate clinical prodrug GS\u20109131. The first basic protocol of this unit details improved procedures for the preparation of 2\u2032\u2010Fd4AP and related phosphonate esters by introduction of a hydroxylmethyl phosphonate ester regioselectively and stereoselectively onto a furanose core via a glycal intermediate. The method described is believed to be robust and flexible, allowing for a variety of analogs with other nucleobases or furanose 2\u2032\u2010ring substitutions to be prepared. The preparation of monoamidate and bisamidate prodrugs either on the phosphonate diacid or its monophenyl ester is then described in the second and third basic protocols of this unit. <jats:italic>Curr. Protoc. Nucleic Acid Chem<\/jats:italic>. 56:14.10.1\u201014.10.21. \u00a9 2014 by John Wiley &amp; Sons, Inc.<\/jats:p>","DOI":"10.1002\/0471142700.nc1410s56","type":"journal-article","created":{"date-parts":[[2014,3,26]],"date-time":"2014-03-26T20:34:01Z","timestamp":1395866041000},"source":"Crossref","is-referenced-by-count":1,"title":["Anti\u2010HIV Nucleoside Phosphonate GS\u20109148 and Its Prodrug GS\u20109131: Scale Up of a 2\u2032\u2010F Modified Cyclic Nucleoside Phosphonate and Synthesis of Selected Amidate Prodrugs"],"prefix":"10.1002","volume":"56","author":[{"given":"Richard L.","family":"Mackman","sequence":"first","affiliation":[{"name":"Gilead Sciences, Inc  Foster City California"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2014,3,26]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.00968-06"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2007.11.125"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1081\/NCN-100002338"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.01215-07"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1080\/07328318908054159"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00166a019"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00008a013"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)91850-1"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm010418n"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.49.5.1898-1906.2005"},{"key":"e_1_2_6_12_1","unstructured":"Mackman R.L.2013.Design and SAR of amidate prodrugs for acyclic and cyclic nucleoside phosphonate antivirals: The discovery of TAF (GS\u20107340) and GS\u20109131.26thInternational Conference on Antiviral Research San Francisco California May 11\u201015."},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2007.10.038"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2007.11.126"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2010.03.041"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00161a041"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/jr9630001149"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/C39790000052"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00483a042"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00081a003"},{"key":"e_1_2_6_21_1","unstructured":"Vemishetti P. Howell H.G. Walker D.G. Brodfuehrer P.R. andShih K.\u2010H.1991.Deoxyfluoronucleoside process. U.S. Patent Application EP0428109A2."},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00764a053"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00987-3"}],"container-title":["Current Protocols in Nucleic Acid Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2F0471142700.nc1410s56","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/0471142700.nc1410s56","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/0471142700.nc1410s56","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/0471142700.nc1410s56","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,20]],"date-time":"2023-08-20T04:31:56Z","timestamp":1692505916000},"score":1,"resource":{"primary":{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/10.1002\/0471142700.nc1410s56"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,3]]},"references-count":22,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2014,3]]}},"alternative-id":["10.1002\/0471142700.nc1410s56"],"URL":"https:\/\/doi.org\/10.1002\/0471142700.nc1410s56","archive":["Portico"],"relation":{},"ISSN":["1934-9270","1934-9289"],"issn-type":[{"value":"1934-9270","type":"print"},{"value":"1934-9289","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,3]]}}}