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PMC:7291971 / 38796-40469 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T796 45-47 CHEBI:30756;CHEBI:30756 denotes 9H
T797 48-58 CHEBI:30756;CHEBI:30756 denotes purin-9-yl
T798 59-83 CHEBI:53233;CHEBI:53233 denotes -2,2-dimethyl-tetrahydro
T799 84-86 CHEBI:53233;CHEBI:53233 denotes 2H
T800 102-104 CHEBI:53233;CHEBI:53233 denotes 3]
T801 104-110 CHEBI:82321;CHEBI:82321 denotes dioxol
T802 110-116 CHEBI:53233;CHEBI:53233 denotes -4-yl]
T803 116-122 CHEBI:29309;CHEBI:29309 denotes methyl
T804 122-123 CHEBI:53233;CHEBI:53233 denotes }
T805 123-128 CHEBI:46882;CHEBI:46882 denotes amino
T806 129-135 CHEBI:42241;CHEBI:42241 denotes ethoxy
T807 137-165 CHEBI:53233;CHEBI:53233 denotes 4-[(tert-butyldimethylsilyl)
T808 165-168 CHEBI:29354;CHEBI:29354 denotes oxy
T809 170-171 CHEBI:53233;CHEBI:53233 denotes 5
T810 179-180 CHEBI:53233;CHEBI:53233 denotes -
T811 180-198 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T812 199-202 CHEBI:29354;CHEBI:29354 denotes oxy
T813 203-209 CHEBI:29309;CHEBI:29309 denotes methyl
T814 210-216 CHEBI:26911;CHEBI:26911 denotes oxolan
T815 216-217 CHEBI:15533;CHEBI:15533 denotes -
T816 217-222 CHEBI:53233;CHEBI:53233 denotes 2-yl]
T817 223-225 CHEBI:53233;CHEBI:53233 denotes 9H
T818 225-231 CHEBI:35589;CHEBI:35589 denotes -purin
T819 232-233 CHEBI:53233;CHEBI:53233 denotes 6
T820 234-239 CHEBI:32952;CHEBI:32952 denotes amine
T821 250-258 CHEBI:75958;CHEBI:75958 denotes solution
T822 329-334 CHEBI:32031;CHEBI:32031 denotes K2CO3
T823 367-377 CHEBI:48498;CHEBI:48498 denotes thiophenol
T824 476-483 CHEBI:60004;CHEBI:60004 denotes mixture
T825 533-540 CHEBI:15377;CHEBI:15377 denotes aqueous
T826 541-545 CHEBI:32145;CHEBI:32145 denotes NaOH
T827 546-554 CHEBI:75958;CHEBI:75958 denotes solution
T828 568-575 CHEBI:15377;CHEBI:15377 denotes aqueous
T829 686-692 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T830 781-787 CHEBI:30563;CHEBI:30563 denotes silica
T831 815-819 CHEBI:32145;CHEBI:32145 denotes MeOH
T832 899-903 CHEBI:32145;CHEBI:32145 denotes MeOH
T833 927-932 CHEBI:30808;CHEBI:30808 denotes CDCl3
T834 1366-1369 CHEBI:36927;CHEBI:36927 denotes 13C
T37264 45-47 CHEBI:30756;CHEBI:30756 denotes 9H
T61516 48-58 CHEBI:30756;CHEBI:30756 denotes purin-9-yl
T43297 59-83 CHEBI:53233;CHEBI:53233 denotes -2,2-dimethyl-tetrahydro
T26849 84-86 CHEBI:53233;CHEBI:53233 denotes 2H
T6291 102-104 CHEBI:53233;CHEBI:53233 denotes 3]
T10899 104-110 CHEBI:82321;CHEBI:82321 denotes dioxol
T30917 110-116 CHEBI:53233;CHEBI:53233 denotes -4-yl]
T29054 116-122 CHEBI:29309;CHEBI:29309 denotes methyl
T91631 122-123 CHEBI:53233;CHEBI:53233 denotes }
T71293 123-128 CHEBI:46882;CHEBI:46882 denotes amino
T48278 129-135 CHEBI:42241;CHEBI:42241 denotes ethoxy
T81026 137-165 CHEBI:53233;CHEBI:53233 denotes 4-[(tert-butyldimethylsilyl)
T93948 165-168 CHEBI:29354;CHEBI:29354 denotes oxy
T43751 170-171 CHEBI:53233;CHEBI:53233 denotes 5
T98761 179-180 CHEBI:53233;CHEBI:53233 denotes -
T36094 180-198 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T18228 199-202 CHEBI:29354;CHEBI:29354 denotes oxy
T76224 203-209 CHEBI:29309;CHEBI:29309 denotes methyl
T41246 210-216 CHEBI:26911;CHEBI:26911 denotes oxolan
T37085 216-217 CHEBI:15533;CHEBI:15533 denotes -
T61179 217-222 CHEBI:53233;CHEBI:53233 denotes 2-yl]
T12065 223-225 CHEBI:53233;CHEBI:53233 denotes 9H
T53177 225-231 CHEBI:35589;CHEBI:35589 denotes -purin
T82206 232-233 CHEBI:53233;CHEBI:53233 denotes 6
T57054 234-239 CHEBI:32952;CHEBI:32952 denotes amine
T10400 250-258 CHEBI:75958;CHEBI:75958 denotes solution
T2918 329-334 CHEBI:32031;CHEBI:32031 denotes K2CO3
T54095 367-377 CHEBI:48498;CHEBI:48498 denotes thiophenol
T6657 476-483 CHEBI:60004;CHEBI:60004 denotes mixture
T33281 533-540 CHEBI:15377;CHEBI:15377 denotes aqueous
T65041 541-545 CHEBI:32145;CHEBI:32145 denotes NaOH
T40366 546-554 CHEBI:75958;CHEBI:75958 denotes solution
T1989 568-575 CHEBI:15377;CHEBI:15377 denotes aqueous
T99804 686-692 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T52387 781-787 CHEBI:30563;CHEBI:30563 denotes silica
T84377 815-819 CHEBI:32145;CHEBI:32145 denotes MeOH
T32932 899-903 CHEBI:32145;CHEBI:32145 denotes MeOH
T16692 927-932 CHEBI:30808;CHEBI:30808 denotes CDCl3
T39500 1366-1369 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
676 307-310 Chemical denotes DMF
677 329-334 Chemical denotes K2CO3 MESH:C037593
678 367-377 Chemical denotes thiophenol MESH:C042983
679 456-461 Chemical denotes argon MESH:D001128
680 501-504 Chemical denotes DCM
681 541-545 Chemical denotes NaOH
682 601-604 Chemical denotes DCM
683 668-673 Chemical denotes brine MESH:C017082
684 686-692 Chemical denotes Na2SO4
685 781-791 Chemical denotes silica gel MESH:D058428
686 815-819 Chemical denotes MeOH
687 823-826 Chemical denotes DCM
688 899-903 Chemical denotes MeOH
689 904-907 Chemical denotes DCM
690 1624-1638 Chemical denotes C37H62N11O7Si2
691 1597-1601 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T286 248-249 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T287 379-381 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T288 634-641 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T289 634-641 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T290 870-871 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T291 1640-1643 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T659 37-58 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T660 39-44 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T661 64-72 Chemical denotes dimethyl http://purl.obolibrary.org/obo/CHEBI_33601|http://purl.obolibrary.org/obo/CHEBI_42266
T663 116-122 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T665 123-128 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T666 129-135 Chemical denotes ethoxy http://purl.obolibrary.org/obo/CHEBI_42241
T667 165-168 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T668 199-202 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T669 203-209 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T671 223-239 Chemical denotes 9H-purin-6-amine http://purl.obolibrary.org/obo/CHEBI_16708
T672 234-239 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T673 250-258 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T674 307-310 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T675 329-334 Chemical denotes K2CO3 http://purl.obolibrary.org/obo/CHEBI_131526
T676 367-377 Chemical denotes thiophenol http://purl.obolibrary.org/obo/CHEBI_48498
T677 456-461 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T678 476-483 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T679 501-504 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T680 541-545 Chemical denotes NaOH http://purl.obolibrary.org/obo/CHEBI_32145
T681 546-554 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T682 601-604 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T683 686-692 Chemical denotes Na2SO4 http://purl.obolibrary.org/obo/CHEBI_32149
T684 781-787 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T685 815-819 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T686 823-826 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T687 885-887 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T688 899-903 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T689 904-907 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T690 910-912 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T691 927-932 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T692 945-947 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T693 959-961 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T694 973-975 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T695 987-989 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T696 1032-1034 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T697 1071-1073 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T698 1090-1092 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T699 1109-1111 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T700 1167-1169 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T701 1207-1209 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T702 1247-1249 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T703 1384-1389 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T7 501-504 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T8 601-604 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T9 823-826 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T10 904-907 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T287 0-244 Sentence denotes 4.1.6 9-[(2R,5R)-3-[2-({[(4R,6R)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d] [1,3]dioxol-4-yl]methyl}amino)ethoxy]-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-9H-purin-6-amine (20)
T288 245-406 Sentence denotes To a solution of 19 (210 mg, 0.20 mmol, 1.00 eq) in anhydrous DMF (10 mL) was added K2CO3 (85 mg, 0.61 mmol, 3.00 eq) and thiophenol (11 μL, 1.14 mmol, 5.70 eq).
T289 407-563 Sentence denotes After stirring for 2 h at room temperature under argon, the reaction mixture was diluted with DCM (20 mL) and washed with 1 M aqueous NaOH solution (10 mL).
T290 564-723 Sentence denotes The aqueous layer was extracted with DCM (3 × 20 mL) and the combined organic extracts were washed with brine, dried over Na2SO4 and concentrated under vacuum.
T291 724-884 Sentence denotes The residue was purified by flash column chromatography (silica gel, linear gradient 0–15% MeOH in DCM) as the eluent to give 20 (129 mg, 76%) as a white solid.
T292 885-909 Sentence denotes Rf 0.31 (8:92 MeOH/DCM).
T293 910-1365 Sentence denotes 1H NMR (500 MHz, CDCl3) δ 8.32 (s, 1H), 8.31 (s, 1H), 8.17 (s, 1H), 7.93 (s, 1H), 6.17–6.06 (m, 5H), 6.03 (d, J = 2.9 Hz, 1H), 5.39 (dd, J = 6.5 Hz, J = 3.0 Hz, 1H), 4.99–4.92 (m, 1H), 4.51–4.45 (m, 1H), 4.33–4.25 (m, 2H), 4.08 (dt, J = 5.6 Hz, J = 3.2 Hz, 1H), 3.98 (dd, J = 11.5 Hz, J = 3.6 Hz, 1H), 3.75 (dd, J = 11.6 Hz, J = 2.8 Hz, 1H), 3.71–3.63 (m, 2H), 2.95–2.69 (m, 4H), 1.61 (s, 3H), 1.37 (s, 3H), 0.92 (s, 9H), 0.88 (s, 9H), 0.13–0.04 (m, 12H).
T294 1366-1596 Sentence denotes 13C NMR (125 MHz, CDCl3) δ 155.8, 155.7, 153.3, 153.1, 149.7, 149.6, 139.8, 139.4, 120.5, 120.3, 114.8, 90.7, 87.2, 85.8, 85.1, 83.9, 82.6, 82.4, 70.3, 70.13, 62.0, 51.5, 49.5, 27.4, 26.2, 25.8, 18.6, 18.2, −4.5, −4.8, −5.2, −5.3.
T295 1597-1646 Sentence denotes HRMS (ESI+): m/z calcd for C37H62N11O7Si2 [M+H]+:
T296 1647-1663 Sentence denotes 828.4372, found:
T297 1664-1673 Sentence denotes 828.4371.