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PMC:7291971 / 42171-44173 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T866 57-58 CHEBI:53233;CHEBI:53233 denotes -
T867 58-62 CHEBI:52029;CHEBI:52029 denotes 2,2-
T868 62-71 CHEBI:53233;CHEBI:53233 denotes dimethyl-
T869 71-81 CHEBI:52029;CHEBI:52029 denotes tetrahydro
T870 81-84 CHEBI:53233;CHEBI:53233 denotes -2H
T871 98-101 CHEBI:52029;CHEBI:52029 denotes 1,3
T872 101-102 CHEBI:53233;CHEBI:53233 denotes ]
T873 102-108 CHEBI:52029;CHEBI:52029 denotes dioxol
T874 108-113 CHEBI:53233;CHEBI:53233 denotes -4-yl
T875 160-169 CHEBI:53233;CHEBI:53233 denotes 4-[(tert-
T876 169-187 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T877 187-188 CHEBI:53233;CHEBI:53233 denotes )
T878 188-191 CHEBI:29354;CHEBI:29354 denotes oxy
T879 191-203 CHEBI:53233;CHEBI:53233 denotes ]-5-{[(tert-
T880 203-221 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T881 221-222 CHEBI:53233;CHEBI:53233 denotes )
T882 222-225 CHEBI:29354;CHEBI:29354 denotes oxy
T883 225-226 CHEBI:53233;CHEBI:53233 denotes ]
T884 226-232 CHEBI:29309;CHEBI:29309 denotes methyl
T885 232-233 CHEBI:53233;CHEBI:53233 denotes }
T886 233-239 CHEBI:26911;CHEBI:26911 denotes oxolan
T887 239-244 CHEBI:53233;CHEBI:53233 denotes -3-yl
T888 245-248 CHEBI:29354;CHEBI:29354 denotes oxy
T889 249-254 CHEBI:37807;CHEBI:37807 denotes ethyl
T890 255-260 CHEBI:46882;CHEBI:46882 denotes amino
T891 275-281 CHEBI:75508;CHEBI:75508 denotes butoxy
T892 282-290 CHEBI:23019;CHEBI:23019 denotes carbonyl
T893 291-296 CHEBI:46882;CHEBI:46882 denotes amino
T894 297-306 CHEBI:17968;CHEBI:17968 denotes butanoate
T895 317-325 CHEBI:75958;CHEBI:75958 denotes solution
T896 395-403 CHEBI:17478;CHEBI:17478 denotes aldehyde
T897 464-475 CHEBI:15366;CHEBI:15366 denotes acetic acid
T898 564-570 CHEBI:35607;CHEBI:35607 denotes sodium
T899 571-592 CHEBI:28621;CHEBI:28621 denotes triacetoxyborohydride
T900 670-677 CHEBI:60004;CHEBI:60004 denotes mixture
T901 733-740 CHEBI:15377;CHEBI:15377 denotes aqueous
T902 741-747 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T903 761-768 CHEBI:15377;CHEBI:15377 denotes aqueous
T904 879-885 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T905 974-980 CHEBI:30563;CHEBI:30563 denotes silica
T906 1007-1011 CHEBI:32145;CHEBI:32145 denotes MeOH
T907 1072-1076 CHEBI:32145;CHEBI:32145 denotes MeOH
T908 1105-1110 CHEBI:30808;CHEBI:30808 denotes CDCl3
T909 1636-1639 CHEBI:36927;CHEBI:36927 denotes 13C
T28859 57-58 CHEBI:53233;CHEBI:53233 denotes -
T41785 58-62 CHEBI:52029;CHEBI:52029 denotes 2,2-
T97314 62-71 CHEBI:53233;CHEBI:53233 denotes dimethyl-
T32713 71-81 CHEBI:52029;CHEBI:52029 denotes tetrahydro
T98800 81-84 CHEBI:53233;CHEBI:53233 denotes -2H
T70619 98-101 CHEBI:52029;CHEBI:52029 denotes 1,3
T56184 101-102 CHEBI:53233;CHEBI:53233 denotes ]
T16818 102-108 CHEBI:52029;CHEBI:52029 denotes dioxol
T71070 108-113 CHEBI:53233;CHEBI:53233 denotes -4-yl
T17264 160-169 CHEBI:53233;CHEBI:53233 denotes 4-[(tert-
T92170 169-187 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T11160 187-188 CHEBI:53233;CHEBI:53233 denotes )
T1841 188-191 CHEBI:29354;CHEBI:29354 denotes oxy
T29745 191-203 CHEBI:53233;CHEBI:53233 denotes ]-5-{[(tert-
T95154 203-221 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T61817 221-222 CHEBI:53233;CHEBI:53233 denotes )
T88971 222-225 CHEBI:29354;CHEBI:29354 denotes oxy
T34714 225-226 CHEBI:53233;CHEBI:53233 denotes ]
T89053 226-232 CHEBI:29309;CHEBI:29309 denotes methyl
T20420 232-233 CHEBI:53233;CHEBI:53233 denotes }
T79823 233-239 CHEBI:26911;CHEBI:26911 denotes oxolan
T49653 239-244 CHEBI:53233;CHEBI:53233 denotes -3-yl
T84503 245-248 CHEBI:29354;CHEBI:29354 denotes oxy
T87203 249-254 CHEBI:37807;CHEBI:37807 denotes ethyl
T18939 255-260 CHEBI:46882;CHEBI:46882 denotes amino
T75533 275-281 CHEBI:75508;CHEBI:75508 denotes butoxy
T37718 282-290 CHEBI:23019;CHEBI:23019 denotes carbonyl
T50416 291-296 CHEBI:46882;CHEBI:46882 denotes amino
T88272 297-306 CHEBI:17968;CHEBI:17968 denotes butanoate
T18742 317-325 CHEBI:75958;CHEBI:75958 denotes solution
T4622 395-403 CHEBI:17478;CHEBI:17478 denotes aldehyde
T82195 464-475 CHEBI:15366;CHEBI:15366 denotes acetic acid
T9375 564-570 CHEBI:35607;CHEBI:35607 denotes sodium
T8158 571-592 CHEBI:28621;CHEBI:28621 denotes triacetoxyborohydride
T27845 670-677 CHEBI:60004;CHEBI:60004 denotes mixture
T73639 733-740 CHEBI:15377;CHEBI:15377 denotes aqueous
T71101 741-747 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T96786 761-768 CHEBI:15377;CHEBI:15377 denotes aqueous
T30010 879-885 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T67189 974-980 CHEBI:30563;CHEBI:30563 denotes silica
T22030 1007-1011 CHEBI:32145;CHEBI:32145 denotes MeOH
T49057 1072-1076 CHEBI:32145;CHEBI:32145 denotes MeOH
T81566 1105-1110 CHEBI:30808;CHEBI:30808 denotes CDCl3
T29671 1636-1639 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
759 374-377 Chemical denotes DCM
760 395-403 Chemical denotes aldehyde MESH:D000447
761 449-452 Chemical denotes DCM
762 464-475 Chemical denotes acetic acid MESH:D019342
763 557-562 Chemical denotes argon MESH:D001128
764 564-592 Chemical denotes sodium triacetoxyborohydride
765 616-618 Chemical denotes eq
766 695-698 Chemical denotes DCM
767 741-747 Chemical denotes NaHCO3 MESH:D017693
768 794-797 Chemical denotes DCM
769 861-866 Chemical denotes brine MESH:C017082
770 879-885 Chemical denotes Na2SO4
771 974-984 Chemical denotes silica gel MESH:D058428
772 1007-1011 Chemical denotes MeOH
773 1015-1018 Chemical denotes DCM
774 1072-1076 Chemical denotes MeOH
775 1077-1080 Chemical denotes DCM
776 1950-1965 Chemical denotes C52H87N12O13Si2
777 1923-1927 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T300 308-310 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T301 315-316 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T302 827-834 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T303 827-834 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T304 1028-1030 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T305 1036-1042 http://purl.obolibrary.org/obo/CLO_0007701 denotes mg, 93
T306 1048-1049 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T307 1967-1970 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T745 35-56 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T746 37-42 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T747 62-70 Chemical denotes dimethyl http://purl.obolibrary.org/obo/CHEBI_33601|http://purl.obolibrary.org/obo/CHEBI_42266
T749 114-120 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T751 137-158 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T752 139-144 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T753 188-191 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T754 222-225 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T755 226-232 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T757 245-248 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T758 249-254 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T760 255-260 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T761 282-290 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T762 291-296 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T763 297-306 Chemical denotes butanoate http://purl.obolibrary.org/obo/CHEBI_17968
T764 317-325 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T765 374-377 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T766 395-403 Chemical denotes aldehyde http://purl.obolibrary.org/obo/CHEBI_17478
T767 449-452 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T768 464-475 Chemical denotes acetic acid http://purl.obolibrary.org/obo/CHEBI_15366
T769 471-475 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T770 557-562 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T771 564-570 Chemical denotes sodium http://purl.obolibrary.org/obo/CHEBI_26708
T772 670-677 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T773 695-698 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T774 741-747 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T775 794-797 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T776 879-885 Chemical denotes Na2SO4 http://purl.obolibrary.org/obo/CHEBI_32149
T777 974-980 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T778 1007-1011 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T779 1015-1018 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T780 1063-1065 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T781 1072-1076 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T782 1077-1080 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T783 1088-1090 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T784 1105-1110 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T785 1123-1125 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T786 1137-1139 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T787 1151-1153 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T788 1165-1167 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T789 1191-1193 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T790 1217-1219 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T791 1270-1272 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T792 1308-1310 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T793 1347-1349 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T794 1366-1368 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T795 1405-1407 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T796 1445-1447 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T797 1521-1523 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T798 1540-1542 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T799 1654-1659 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T12 374-377 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T13 449-452 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T14 695-698 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T15 794-797 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T16 1015-1018 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T17 1077-1080 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T311 0-311 Sentence denotes 4.1.9 Methyl (2S)-4-({[(4R,6R)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d] [1,3]dioxol-4-yl]methyl}(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-3-yl]oxy}ethyl)amino)-2-{bis[(tert-butoxy)carbonyl]amino}butanoate (22)
T312 312-504 Sentence denotes To a solution of 20 (250 mg, 0.30 mmol, 1.00 eq) in anhydrous DCM (9 mL) was added aldehyde 21 (120 mg, 0.36 mmol, 1.20 eq) in anhydrous DCM (9 mL) and acetic acid (20 μL, 0.36 mmol, 1.20 eq).
T313 505-630 Sentence denotes After stirring for 20 min at room temperature under argon, sodium triacetoxyborohydride (96 mg, 0.45 mmol, 1.5 eq) was added.
T314 631-756 Sentence denotes After stirring for 2.5 h, the reaction mixture was diluted with DCM (30 mL) and washed with saturated aqueous NaHCO3 (30 mL).
T315 757-916 Sentence denotes The aqueous layer was extracted with DCM (3 × 30 mL) and the combined organic extracts were washed with brine, dried over Na2SO4 and concentrated under vacuum.
T316 917-1062 Sentence denotes The residue was purified by flash column chromatography (silica gel, linear gradient 0–8% MeOH in DCM) to give 22 (321 mg, 93%) as a white solid.
T317 1063-1087 Sentence denotes Rf 0.71 (MeOH/DCM 5:95).
T318 1088-1635 Sentence denotes 1H NMR (600 MHz, CDCl3) δ 8.33 (s, 1H), 8.30 (s, 1H), 8.17 (s, 1H), 7.93 (s, 1H), 6.09 (d, J = 3.3 Hz, 1H), 6.01 (d, J = 2.4 Hz, 1H), 5.97 (m, 4H), 5.42 (dd, J = 6.5 Hz, J = 2.4 Hz, 1H), 4.93–4.86 (m, 2H), 4.54–4.49 (m, 1H), 4.33 (td, J = 6.8 Hz, J = 3.3 Hz, 1H), 4.29–4.24 (m, 1H), 4.08 (dt, J = 6.2 Hz, J = 3.2 Hz, 1H), 3.99 (dd, J = 11.5 Hz, J = 3.7 Hz, 1H), 3.78–3.63 (m, 6H), 2.84–2.74 (m, 3H), 2.71–2.51 (m, 3H), 2.33–2.23 (m, 1H), 1.91–1.82 (m, 1H), 1.58 (s, 3H), 1.46 (s, 18H), 1.36 (s, 3H), 0.91 (s, 9H), 0.90 (s, 9H), 0.10–0.05 (m, 12H).
T319 1636-1922 Sentence denotes 13C NMR (125 MHz, CDCl3) δ 171.6, 155.8, 155.7, 153.3, 153.2, 152.3, 149.7, 149.5, 140.1, 139.8, 120.5, 120.4, 114.5, 91.1, 87.4, 85.45, 84.8, 84.1, 83.3, 83.3, 82.5, 69.9, 69.1, 61.9, 56.3, 56.3, 53.7, 52.4, 52.1, 28.1, 28.1, 27.3, 26.2, 26.0, 25.6, 18.7, 18.3, −4.3, −4.6, −5.2, −5.2.
T320 1923-1973 Sentence denotes HRMS (ESI+): m/z calcd for C52H87N12O13Si2 [M+H]+:
T321 1974-1991 Sentence denotes 1143.6049, found:
T322 1992-2002 Sentence denotes 1143.6043.