PMC:7291971 / 82396-83725 JSONTXT

{"project":"LitCovid-PMC-OGER-BB","denotations":[{"id":"T1640","span":{"begin":63,"end":64},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T1641","span":{"begin":69,"end":72},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T1642","span":{"begin":73,"end":83},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T1643","span":{"begin":85,"end":87},"obj":"CHEBI:34018;CHEBI:34018"},{"id":"T1644","span":{"begin":87,"end":94},"obj":"CHEBI:43176;CHEBI:43176"},{"id":"T1645","span":{"begin":98,"end":111},"obj":"CHEBI:24712;CHEBI:24712"},{"id":"T1646","span":{"begin":112,"end":118},"obj":"CHEBI:26911;CHEBI:26911"},{"id":"T1647","span":{"begin":118,"end":119},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T1648","span":{"begin":119,"end":120},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1649","span":{"begin":120,"end":123},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T1650","span":{"begin":123,"end":124},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1651","span":{"begin":124,"end":127},"obj":"CHEBI:29354;CHEBI:29354"},{"id":"T1652","span":{"begin":128,"end":133},"obj":"CHEBI:37807;CHEBI:37807"},{"id":"T1653","span":{"begin":136,"end":138},"obj":"CHEBI:86228;CHEBI:86228"},{"id":"T1654","span":{"begin":138,"end":144},"obj":"CHEBI:47853;CHEBI:47853"},{"id":"T1655","span":{"begin":144,"end":158},"obj":"CHEBI:86228;CHEBI:86228"},{"id":"T1656","span":{"begin":159,"end":165},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T1657","span":{"begin":166,"end":171},"obj":"CHEBI:46882;CHEBI:46882"},{"id":"T1658","span":{"begin":172,"end":178},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T1659","span":{"begin":179,"end":186},"obj":"CHEBI:26911;CHEBI:26911"},{"id":"T1660","span":{"begin":187,"end":189},"obj":"CHEBI:52029;CHEBI:52029"},{"id":"T1661","span":{"begin":189,"end":191},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1662","span":{"begin":191,"end":195},"obj":"CHEBI:23824;CHEBI:23824"},{"id":"T1663","span":{"begin":284,"end":296},"obj":"CHEBI:38472;CHEBI:38472"},{"id":"T1664","span":{"begin":1037,"end":1040},"obj":"CHEBI:36927;CHEBI:36927"},{"id":"T41134","span":{"begin":63,"end":64},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T27334","span":{"begin":69,"end":72},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T20136","span":{"begin":73,"end":83},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T73618","span":{"begin":85,"end":87},"obj":"CHEBI:34018;CHEBI:34018"},{"id":"T76408","span":{"begin":87,"end":94},"obj":"CHEBI:43176;CHEBI:43176"},{"id":"T70567","span":{"begin":98,"end":111},"obj":"CHEBI:24712;CHEBI:24712"},{"id":"T85384","span":{"begin":112,"end":118},"obj":"CHEBI:26911;CHEBI:26911"},{"id":"T6101","span":{"begin":118,"end":119},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T32228","span":{"begin":119,"end":120},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T62461","span":{"begin":120,"end":123},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T28904","span":{"begin":123,"end":124},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T40535","span":{"begin":124,"end":127},"obj":"CHEBI:29354;CHEBI:29354"},{"id":"T45088","span":{"begin":128,"end":133},"obj":"CHEBI:37807;CHEBI:37807"},{"id":"T66662","span":{"begin":136,"end":138},"obj":"CHEBI:86228;CHEBI:86228"},{"id":"T71841","span":{"begin":138,"end":144},"obj":"CHEBI:47853;CHEBI:47853"},{"id":"T70937","span":{"begin":144,"end":158},"obj":"CHEBI:86228;CHEBI:86228"},{"id":"T41213","span":{"begin":159,"end":165},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T22878","span":{"begin":166,"end":171},"obj":"CHEBI:46882;CHEBI:46882"},{"id":"T6558","span":{"begin":172,"end":178},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T11187","span":{"begin":179,"end":186},"obj":"CHEBI:26911;CHEBI:26911"},{"id":"T58590","span":{"begin":187,"end":189},"obj":"CHEBI:52029;CHEBI:52029"},{"id":"T86321","span":{"begin":189,"end":191},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T9071","span":{"begin":191,"end":195},"obj":"CHEBI:23824;CHEBI:23824"},{"id":"T84625","span":{"begin":284,"end":296},"obj":"CHEBI:38472;CHEBI:38472"},{"id":"T93629","span":{"begin":1037,"end":1040},"obj":"CHEBI:36927;CHEBI:36927"}],"text":"4.1.38 (2R,5R)-2-(6-amino-9H-purin-9-yl)-5-{[(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)[(4-chloro-3-nitrophenyl)methyl]amino]methyl}oxolane-3,4-diol (15)\nUsing method C with 35 (140 mg, 0.14 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 15 (25 mg, 25%) was obtained as a white powder with 99% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.35 (s, 1H), 8.23 (s, 1H), 8.11 (s, 1H), 8.07 (s, 1H), 7.89 (d, J = 1.9 Hz, 1H), 7.50 (d, J = 8.3 Hz, 1H), 7.45 (dd, J = 8.3 Hz, J = 2.0 Hz, 1H), 7.32 (br. s, 2H), 7.24 (br. s, 2H), 5.99 (d, J = 5.9 Hz, 1H), 5.83 (d, J = 5.1 Hz, 1H), 5.51–5.32 (m, 2H), 5.24 (br. s, 1H), 5.13 (br. s, 1H), 4.57 (t, J = 5.2 Hz, 1H), 4.45 (dd, J = 6.1 Hz, J = 4.8 Hz, 1H), 4.30 (t, J = 4.1 Hz, 1H), 4.05 (t, J = 5.0 Hz, 1H), 4.02–3.95 (m, 2H), 3.73–3.63 (m, 4H), 3.58–3.51 (m, 2H), 2.83 (dd, J = 14.0 Hz, J = 4.4 Hz, 1H), 2.73 (dd, J = 14.0 Hz, J = 7.2 Hz, 1H), 2.69–2.63 (m, 2H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.5 (2C), 149.3, 148.9, 147.2, 140.1, 139.8, 139.6, 133.7, 131.0, 125.0, 122.9, 119.3, 119.2, 87.8, 86.2, 86.1, 82.2, 81.3, 72.4, 71.8, 68.9, 68.1, 61.3, 56.8, 56.0, 53.0. HRMS (ESI+): m/z calcd for C29H34N12O9Cl [M+H]+: 729.2255, Found 729.2256."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1556","span":{"begin":284,"end":296},"obj":"Chemical"},{"id":"1557","span":{"begin":300,"end":305},"obj":"Chemical"},{"id":"1558","span":{"begin":445,"end":447},"obj":"Chemical"},{"id":"1559","span":{"begin":462,"end":468},"obj":"Chemical"},{"id":"1560","span":{"begin":483,"end":485},"obj":"Chemical"},{"id":"1561","span":{"begin":497,"end":499},"obj":"Chemical"},{"id":"1562","span":{"begin":511,"end":513},"obj":"Chemical"},{"id":"1563","span":{"begin":525,"end":527},"obj":"Chemical"},{"id":"1564","span":{"begin":551,"end":553},"obj":"Chemical"},{"id":"1565","span":{"begin":577,"end":579},"obj":"Chemical"},{"id":"1566","span":{"begin":616,"end":618},"obj":"Chemical"},{"id":"1567","span":{"begin":634,"end":636},"obj":"Chemical"},{"id":"1568","span":{"begin":652,"end":654},"obj":"Chemical"},{"id":"1569","span":{"begin":678,"end":680},"obj":"Chemical"},{"id":"1570","span":{"begin":704,"end":706},"obj":"Chemical"},{"id":"1571","span":{"begin":723,"end":725},"obj":"Chemical"},{"id":"1572","span":{"begin":1255,"end":1259},"obj":"Disease"},{"id":"1573","span":{"begin":1282,"end":1291},"obj":"CellLine"}],"attributes":[{"id":"A1556","pred":"tao:has_database_id","subj":"1556","obj":"MESH:C032159"},{"id":"A1567","pred":"tao:has_database_id","subj":"1567","obj":"MESH:D003903"},{"id":"A1568","pred":"tao:has_database_id","subj":"1568","obj":"MESH:D003903"},{"id":"A1571","pred":"tao:has_database_id","subj":"1571","obj":"MESH:D003903"},{"id":"A1573","pred":"tao:has_database_id","subj":"1573","obj":"CVCL:0189"}],"namespaces":[{"prefix":"Tax","uri":"https://www.ncbi.nlm.nih.gov/taxonomy/"},{"prefix":"MESH","uri":"https://id.nlm.nih.gov/mesh/"},{"prefix":"Gene","uri":"https://www.ncbi.nlm.nih.gov/gene/"},{"prefix":"CVCL","uri":"https://web.expasy.org/cellosaurus/CVCL_"}],"text":"4.1.38 (2R,5R)-2-(6-amino-9H-purin-9-yl)-5-{[(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)[(4-chloro-3-nitrophenyl)methyl]amino]methyl}oxolane-3,4-diol (15)\nUsing method C with 35 (140 mg, 0.14 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 15 (25 mg, 25%) was obtained as a white powder with 99% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.35 (s, 1H), 8.23 (s, 1H), 8.11 (s, 1H), 8.07 (s, 1H), 7.89 (d, J = 1.9 Hz, 1H), 7.50 (d, J = 8.3 Hz, 1H), 7.45 (dd, J = 8.3 Hz, J = 2.0 Hz, 1H), 7.32 (br. s, 2H), 7.24 (br. s, 2H), 5.99 (d, J = 5.9 Hz, 1H), 5.83 (d, J = 5.1 Hz, 1H), 5.51–5.32 (m, 2H), 5.24 (br. s, 1H), 5.13 (br. s, 1H), 4.57 (t, J = 5.2 Hz, 1H), 4.45 (dd, J = 6.1 Hz, J = 4.8 Hz, 1H), 4.30 (t, J = 4.1 Hz, 1H), 4.05 (t, J = 5.0 Hz, 1H), 4.02–3.95 (m, 2H), 3.73–3.63 (m, 4H), 3.58–3.51 (m, 2H), 2.83 (dd, J = 14.0 Hz, J = 4.4 Hz, 1H), 2.73 (dd, J = 14.0 Hz, J = 7.2 Hz, 1H), 2.69–2.63 (m, 2H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.5 (2C), 149.3, 148.9, 147.2, 140.1, 139.8, 139.6, 133.7, 131.0, 125.0, 122.9, 119.3, 119.2, 87.8, 86.2, 86.1, 82.2, 81.3, 72.4, 71.8, 68.9, 68.1, 61.3, 56.8, 56.0, 53.0. HRMS (ESI+): m/z calcd for C29H34N12O9Cl [M+H]+: 729.2255, Found 729.2256."}

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T433","span":{"begin":221,"end":223},"obj":"http://purl.obolibrary.org/obo/CLO_0001000"},{"id":"T434","span":{"begin":257,"end":258},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T435","span":{"begin":375,"end":376},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T436","span":{"begin":1297,"end":1300},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"4.1.38 (2R,5R)-2-(6-amino-9H-purin-9-yl)-5-{[(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)[(4-chloro-3-nitrophenyl)methyl]amino]methyl}oxolane-3,4-diol (15)\nUsing method C with 35 (140 mg, 0.14 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 15 (25 mg, 25%) was obtained as a white powder with 99% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.35 (s, 1H), 8.23 (s, 1H), 8.11 (s, 1H), 8.07 (s, 1H), 7.89 (d, J = 1.9 Hz, 1H), 7.50 (d, J = 8.3 Hz, 1H), 7.45 (dd, J = 8.3 Hz, J = 2.0 Hz, 1H), 7.32 (br. s, 2H), 7.24 (br. s, 2H), 5.99 (d, J = 5.9 Hz, 1H), 5.83 (d, J = 5.1 Hz, 1H), 5.51–5.32 (m, 2H), 5.24 (br. s, 1H), 5.13 (br. s, 1H), 4.57 (t, J = 5.2 Hz, 1H), 4.45 (dd, J = 6.1 Hz, J = 4.8 Hz, 1H), 4.30 (t, J = 4.1 Hz, 1H), 4.05 (t, J = 5.0 Hz, 1H), 4.02–3.95 (m, 2H), 3.73–3.63 (m, 4H), 3.58–3.51 (m, 2H), 2.83 (dd, J = 14.0 Hz, J = 4.4 Hz, 1H), 2.73 (dd, J = 14.0 Hz, J = 7.2 Hz, 1H), 2.69–2.63 (m, 2H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.5 (2C), 149.3, 148.9, 147.2, 140.1, 139.8, 139.6, 133.7, 131.0, 125.0, 122.9, 119.3, 119.2, 87.8, 86.2, 86.1, 82.2, 81.3, 72.4, 71.8, 68.9, 68.1, 61.3, 56.8, 56.0, 53.0. HRMS (ESI+): m/z calcd for C29H34N12O9Cl [M+H]+: 729.2255, Found 729.2256."}

{"project":"LitCovid-PD-CHEBI","denotations":[{"id":"T86710","span":{"begin":19,"end":40},"obj":"Chemical"},{"id":"T27946","span":{"begin":21,"end":26},"obj":"Chemical"},{"id":"T88225","span":{"begin":62,"end":83},"obj":"Chemical"},{"id":"T59442","span":{"begin":64,"end":69},"obj":"Chemical"},{"id":"T63219","span":{"begin":87,"end":94},"obj":"Chemical"},{"id":"T81617","span":{"begin":98,"end":111},"obj":"Chemical"},{"id":"T879","span":{"begin":124,"end":127},"obj":"Chemical"},{"id":"T43726","span":{"begin":128,"end":133},"obj":"Chemical"},{"id":"T90371","span":{"begin":138,"end":144},"obj":"Chemical"},{"id":"T8173","span":{"begin":159,"end":165},"obj":"Chemical"},{"id":"T14707","span":{"begin":166,"end":171},"obj":"Chemical"},{"id":"T886","span":{"begin":172,"end":178},"obj":"Chemical"},{"id":"T7921","span":{"begin":179,"end":186},"obj":"Chemical"},{"id":"T64135","span":{"begin":191,"end":195},"obj":"Chemical"},{"id":"T33619","span":{"begin":284,"end":296},"obj":"Chemical"},{"id":"T65501","span":{"begin":306,"end":312},"obj":"Chemical"},{"id":"T98605","span":{"begin":445,"end":447},"obj":"Chemical"},{"id":"T15635","span":{"begin":462,"end":466},"obj":"Chemical"},{"id":"T86380","span":{"begin":483,"end":485},"obj":"Chemical"},{"id":"T23466","span":{"begin":497,"end":499},"obj":"Chemical"},{"id":"T27783","span":{"begin":511,"end":513},"obj":"Chemical"},{"id":"T5803","span":{"begin":525,"end":527},"obj":"Chemical"},{"id":"T88932","span":{"begin":551,"end":553},"obj":"Chemical"},{"id":"T47259","span":{"begin":577,"end":579},"obj":"Chemical"},{"id":"T12853","span":{"begin":616,"end":618},"obj":"Chemical"},{"id":"T31063","span":{"begin":678,"end":680},"obj":"Chemical"},{"id":"T68349","span":{"begin":704,"end":706},"obj":"Chemical"},{"id":"T97689","span":{"begin":741,"end":743},"obj":"Chemical"},{"id":"T19922","span":{"begin":759,"end":761},"obj":"Chemical"},{"id":"T74221","span":{"begin":785,"end":787},"obj":"Chemical"},{"id":"T15952","span":{"begin":824,"end":826},"obj":"Chemical"},{"id":"T45027","span":{"begin":850,"end":852},"obj":"Chemical"},{"id":"T58681","span":{"begin":876,"end":878},"obj":"Chemical"},{"id":"T91299","span":{"begin":973,"end":975},"obj":"Chemical"},{"id":"T20981","span":{"begin":1013,"end":1015},"obj":"Chemical"},{"id":"T94908","span":{"begin":1055,"end":1059},"obj":"Chemical"}],"attributes":[{"id":"A9458","pred":"chebi_id","subj":"T86710","obj":"http://purl.obolibrary.org/obo/CHEBI_30756"},{"id":"A5331","pred":"chebi_id","subj":"T27946","obj":"http://purl.obolibrary.org/obo/CHEBI_46882"},{"id":"A76288","pred":"chebi_id","subj":"T88225","obj":"http://purl.obolibrary.org/obo/CHEBI_30756"},{"id":"A96848","pred":"chebi_id","subj":"T59442","obj":"http://purl.obolibrary.org/obo/CHEBI_46882"},{"id":"A53128","pred":"chebi_id","subj":"T63219","obj":"http://purl.obolibrary.org/obo/CHEBI_43176"},{"id":"A38267","pred":"chebi_id","subj":"T81617","obj":"http://purl.obolibrary.org/obo/CHEBI_24712"},{"id":"A90802","pred":"chebi_id","subj":"T879","obj":"http://purl.obolibrary.org/obo/CHEBI_29354"},{"id":"A18929","pred":"chebi_id","subj":"T43726","obj":"http://purl.obolibrary.org/obo/CHEBI_37807"},{"id":"A79039","pred":"chebi_id","subj":"T43726","obj":"http://purl.obolibrary.org/obo/CHEBI_62801"},{"id":"A83362","pred":"chebi_id","subj":"T90371","obj":"http://purl.obolibrary.org/obo/CHEBI_47853"},{"id":"A35145","pred":"chebi_id","subj":"T8173","obj":"http://purl.obolibrary.org/obo/CHEBI_32875"},{"id":"A79056","pred":"chebi_id","subj":"T8173","obj":"http://purl.obolibrary.org/obo/CHEBI_29309"},{"id":"A96950","pred":"chebi_id","subj":"T14707","obj":"http://purl.obolibrary.org/obo/CHEBI_46882"},{"id":"A69928","pred":"chebi_id","subj":"T886","obj":"http://purl.obolibrary.org/obo/CHEBI_32875"},{"id":"A54270","pred":"chebi_id","subj":"T886","obj":"http://purl.obolibrary.org/obo/CHEBI_29309"},{"id":"A12277","pred":"chebi_id","subj":"T7921","obj":"http://purl.obolibrary.org/obo/CHEBI_26911"},{"id":"A43884","pred":"chebi_id","subj":"T64135","obj":"http://purl.obolibrary.org/obo/CHEBI_23824"},{"id":"A18521","pred":"chebi_id","subj":"T33619","obj":"http://purl.obolibrary.org/obo/CHEBI_38472"},{"id":"A66186","pred":"chebi_id","subj":"T65501","obj":"http://purl.obolibrary.org/obo/CHEBI_35225"},{"id":"A28175","pred":"chebi_id","subj":"T98605","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A54290","pred":"chebi_id","subj":"T15635","obj":"http://purl.obolibrary.org/obo/CHEBI_28262"},{"id":"A95884","pred":"chebi_id","subj":"T86380","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A6576","pred":"chebi_id","subj":"T23466","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A48611","pred":"chebi_id","subj":"T27783","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A1998","pred":"chebi_id","subj":"T5803","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A5942","pred":"chebi_id","subj":"T88932","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A54234","pred":"chebi_id","subj":"T47259","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A5354","pred":"chebi_id","subj":"T12853","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A38759","pred":"chebi_id","subj":"T31063","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A88466","pred":"chebi_id","subj":"T68349","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A32796","pred":"chebi_id","subj":"T97689","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A80962","pred":"chebi_id","subj":"T19922","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A67987","pred":"chebi_id","subj":"T74221","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A18616","pred":"chebi_id","subj":"T15952","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A93131","pred":"chebi_id","subj":"T45027","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A56673","pred":"chebi_id","subj":"T58681","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A5382","pred":"chebi_id","subj":"T91299","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A86585","pred":"chebi_id","subj":"T20981","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A64708","pred":"chebi_id","subj":"T94908","obj":"http://purl.obolibrary.org/obo/CHEBI_28262"}],"text":"4.1.38 (2R,5R)-2-(6-amino-9H-purin-9-yl)-5-{[(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)[(4-chloro-3-nitrophenyl)methyl]amino]methyl}oxolane-3,4-diol (15)\nUsing method C with 35 (140 mg, 0.14 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 15 (25 mg, 25%) was obtained as a white powder with 99% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.35 (s, 1H), 8.23 (s, 1H), 8.11 (s, 1H), 8.07 (s, 1H), 7.89 (d, J = 1.9 Hz, 1H), 7.50 (d, J = 8.3 Hz, 1H), 7.45 (dd, J = 8.3 Hz, J = 2.0 Hz, 1H), 7.32 (br. s, 2H), 7.24 (br. s, 2H), 5.99 (d, J = 5.9 Hz, 1H), 5.83 (d, J = 5.1 Hz, 1H), 5.51–5.32 (m, 2H), 5.24 (br. s, 1H), 5.13 (br. s, 1H), 4.57 (t, J = 5.2 Hz, 1H), 4.45 (dd, J = 6.1 Hz, J = 4.8 Hz, 1H), 4.30 (t, J = 4.1 Hz, 1H), 4.05 (t, J = 5.0 Hz, 1H), 4.02–3.95 (m, 2H), 3.73–3.63 (m, 4H), 3.58–3.51 (m, 2H), 2.83 (dd, J = 14.0 Hz, J = 4.4 Hz, 1H), 2.73 (dd, J = 14.0 Hz, J = 7.2 Hz, 1H), 2.69–2.63 (m, 2H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.5 (2C), 149.3, 148.9, 147.2, 140.1, 139.8, 139.6, 133.7, 131.0, 125.0, 122.9, 119.3, 119.2, 87.8, 86.2, 86.1, 82.2, 81.3, 72.4, 71.8, 68.9, 68.1, 61.3, 56.8, 56.0, 53.0. HRMS (ESI+): m/z calcd for C29H34N12O9Cl [M+H]+: 729.2255, Found 729.2256."}

{"project":"LitCovid-sentences","denotations":[{"id":"T546","span":{"begin":0,"end":200},"obj":"Sentence"},{"id":"T547","span":{"begin":201,"end":444},"obj":"Sentence"},{"id":"T548","span":{"begin":445,"end":1036},"obj":"Sentence"},{"id":"T549","span":{"begin":1037,"end":1254},"obj":"Sentence"},{"id":"T550","span":{"begin":1255,"end":1303},"obj":"Sentence"},{"id":"T551","span":{"begin":1304,"end":1329},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"4.1.38 (2R,5R)-2-(6-amino-9H-purin-9-yl)-5-{[(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)[(4-chloro-3-nitrophenyl)methyl]amino]methyl}oxolane-3,4-diol (15)\nUsing method C with 35 (140 mg, 0.14 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 15 (25 mg, 25%) was obtained as a white powder with 99% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.35 (s, 1H), 8.23 (s, 1H), 8.11 (s, 1H), 8.07 (s, 1H), 7.89 (d, J = 1.9 Hz, 1H), 7.50 (d, J = 8.3 Hz, 1H), 7.45 (dd, J = 8.3 Hz, J = 2.0 Hz, 1H), 7.32 (br. s, 2H), 7.24 (br. s, 2H), 5.99 (d, J = 5.9 Hz, 1H), 5.83 (d, J = 5.1 Hz, 1H), 5.51–5.32 (m, 2H), 5.24 (br. s, 1H), 5.13 (br. s, 1H), 4.57 (t, J = 5.2 Hz, 1H), 4.45 (dd, J = 6.1 Hz, J = 4.8 Hz, 1H), 4.30 (t, J = 4.1 Hz, 1H), 4.05 (t, J = 5.0 Hz, 1H), 4.02–3.95 (m, 2H), 3.73–3.63 (m, 4H), 3.58–3.51 (m, 2H), 2.83 (dd, J = 14.0 Hz, J = 4.4 Hz, 1H), 2.73 (dd, J = 14.0 Hz, J = 7.2 Hz, 1H), 2.69–2.63 (m, 2H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.5 (2C), 149.3, 148.9, 147.2, 140.1, 139.8, 139.6, 133.7, 131.0, 125.0, 122.9, 119.3, 119.2, 87.8, 86.2, 86.1, 82.2, 81.3, 72.4, 71.8, 68.9, 68.1, 61.3, 56.8, 56.0, 53.0. HRMS (ESI+): m/z calcd for C29H34N12O9Cl [M+H]+: 729.2255, Found 729.2256."}