{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,7,30]],"date-time":"2025-07-30T09:45:40Z","timestamp":1753868740281,"version":"3.41.2"},"reference-count":13,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2022,11,28]],"date-time":"2022-11-28T00:00:00Z","timestamp":1669593600000},"content-version":"vor","delay-in-days":27,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Current Protocols"],"published-print":{"date-parts":[[2022,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We present an improved synthesis of (<jats:italic>S<\/jats:italic>)\u2010HPMPA (<jats:bold>1<\/jats:bold>) from an easily accessible and commercially available compound, (<jats:italic>S<\/jats:italic>)\u20103\u2010(benzyloxy)propane\u20101,2\u2010diol (<jats:bold>10<\/jats:bold>). Tritylation of primary alcohol <jats:bold>10<\/jats:bold> was highly selective, and pure product was isolated in good yield. Alkylation of (<jats:italic>R<\/jats:italic>)\u20101\u2010(benzyloxy)\u20103\u2010(trityloxy)propan\u20102\u2010ol (<jats:bold>11<\/jats:bold>) with diethyl <jats:italic>p<\/jats:italic>\u2010toluenesulfonyloxymethyl phosphonate (<jats:bold>6<\/jats:bold>) using sodium hydride in tetrahydrofuran followed by detritylation afforded the desired chiral synthon <jats:bold>12<\/jats:bold>. Tosylation of the primary alcohol and subsequent reaction with sodium adeninate afforded protected <jats:italic>S<\/jats:italic>\u2010HPMPA (<jats:bold>14<\/jats:bold>). Global deprotection using concentrated hydrochloric acid in a sealed tube afforded <jats:italic>S<\/jats:italic>\u2010HPMA (<jats:bold>1<\/jats:bold>), and the deprotected <jats:bold>1<\/jats:bold> was crystallized from water and acetone to obtain a 99% pure product. \u00a9 2022 Wiley Periodicals LLC.<\/jats:p><jats:p><jats:bold>Basic Protocol 1<\/jats:bold>: Preparation of (<jats:italic>R<\/jats:italic>)\u20101\u2010(benzyloxy)\u20103\u2010(trityloxy)propan\u20102\u2010ol (<jats:bold>11<\/jats:bold>)<\/jats:p><jats:p><jats:bold>Basic Protocol 2<\/jats:bold>: Preparation of diethyl (<jats:italic>S<\/jats:italic>)\u2010(((1\u2010(benzyloxy)\u20103\u2010hydroxypropan\u20102\u2010yl)oxy)methyl)phosphonate (<jats:bold>12<\/jats:bold>)<\/jats:p><jats:p><jats:bold>Basic Protocol 3<\/jats:bold>: Preparation of (<jats:italic>R<\/jats:italic>)\u20103\u2010(benzyloxy)\u20102\u2010((diethoxyphosphoryl)methoxy)propyl\u20104\u2010methylbenzenesulfonate (<jats:bold>13<\/jats:bold>)<\/jats:p><jats:p><jats:bold>Basic Protocol 4<\/jats:bold>: Preparation of diethyl (<jats:italic>S<\/jats:italic>)\u2010(((1\u2010(6\u2010amino\u20109<jats:italic>H<\/jats:italic>\u2010purin\u20109\u2010yl)\u20103\u2010(benzyloxy)propan\u20102\u2010yl)oxy)methyl)phosphonate (<jats:bold>14<\/jats:bold>)<\/jats:p><jats:p><jats:bold>Support Protocol 1<\/jats:bold>: Preparation of sodium adeninate<\/jats:p><jats:p><jats:bold>Basic Protocol 5<\/jats:bold>: Preparation of (<jats:italic>S<\/jats:italic>)\u2010(((1\u2010(6\u2010amino\u20109<jats:italic>H<\/jats:italic>\u2010purin\u20109\u2010yl)\u20103\u2010hydroxypropan\u20102\u2010yl)oxy)methyl)phosphonic acid (<jats:bold>1<\/jats:bold>)<\/jats:p>","DOI":"10.1002\/cpz1.602","type":"journal-article","created":{"date-parts":[[2022,11,28]],"date-time":"2022-11-28T14:26:01Z","timestamp":1669645561000},"source":"Crossref","is-referenced-by-count":0,"title":["An Improved Scalable Synthesis of the Potent Antiviral (<i>S<\/i>)\u2010HPMPA"],"prefix":"10.1002","volume":"2","author":[{"given":"Racherla Kishore","family":"Kumar","sequence":"first","affiliation":[{"name":"Sapala Organics Pvt. Ltd  Hyderabad Telangana India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yogesh S.","family":"Sanghvi","sequence":"additional","affiliation":[{"name":"Sapala Organics Pvt. Ltd  Hyderabad Telangana India"},{"name":"Rasayan Inc.  Encinitas California USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paidi Yella","family":"Reddy","sequence":"additional","affiliation":[{"name":"Sapala Organics Pvt. Ltd  Hyderabad Telangana India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shyamapada","family":"Banerjee","sequence":"additional","affiliation":[{"name":"Sapala Organics Pvt. Ltd  Hyderabad Telangana India"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,11,28]]},"reference":[{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/s0166\u20103542(02)00196\u20101"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd1877"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/323464a0"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/s0166\u20103542(87)80004\u20109"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1135\/cccc19872775"},{"key":"e_1_2_10_7_1","unstructured":"Hol\u00fd A. Rosenberg I. &Slama K.(1987).Isomeric O\u2010phosphonylmethyl derivatives of enantiomeric and racemic 9\u2010(2 3\u2010dihydroxypropyl)adenine. U.S. patent 4 659 825."},{"key":"e_1_2_10_8_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.47.7.2193\u20102198.2003"},{"key":"e_1_2_10_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.8b00079"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/0471142700.nca03ds34"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo071181r"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)96670\u2010X"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1080\/07328318908054202"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2003.12.107"}],"container-title":["Current Protocols"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cpz1.602","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cpz1.602","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cpz1.602","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,19]],"date-time":"2023-08-19T09:27:11Z","timestamp":1692437231000},"score":1,"resource":{"primary":{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/10.1002\/cpz1.602"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,11]]},"references-count":13,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2022,11]]}},"alternative-id":["10.1002\/cpz1.602"],"URL":"https:\/\/doi.org\/10.1002\/cpz1.602","archive":["Portico"],"relation":{},"ISSN":["2691-1299","2691-1299"],"issn-type":[{"type":"print","value":"2691-1299"},{"type":"electronic","value":"2691-1299"}],"subject":[],"published":{"date-parts":[[2022,11]]},"article-number":"e602"}}