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PMC:7291971 / 42483-44173 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T895 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T896 83-91 CHEBI:17478;CHEBI:17478 denotes aldehyde
T897 152-163 CHEBI:15366;CHEBI:15366 denotes acetic acid
T898 252-258 CHEBI:35607;CHEBI:35607 denotes sodium
T899 259-280 CHEBI:28621;CHEBI:28621 denotes triacetoxyborohydride
T900 358-365 CHEBI:60004;CHEBI:60004 denotes mixture
T901 421-428 CHEBI:15377;CHEBI:15377 denotes aqueous
T902 429-435 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T903 449-456 CHEBI:15377;CHEBI:15377 denotes aqueous
T904 567-573 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T905 662-668 CHEBI:30563;CHEBI:30563 denotes silica
T906 695-699 CHEBI:32145;CHEBI:32145 denotes MeOH
T907 760-764 CHEBI:32145;CHEBI:32145 denotes MeOH
T908 793-798 CHEBI:30808;CHEBI:30808 denotes CDCl3
T909 1324-1327 CHEBI:36927;CHEBI:36927 denotes 13C
T18742 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T4622 83-91 CHEBI:17478;CHEBI:17478 denotes aldehyde
T82195 152-163 CHEBI:15366;CHEBI:15366 denotes acetic acid
T9375 252-258 CHEBI:35607;CHEBI:35607 denotes sodium
T8158 259-280 CHEBI:28621;CHEBI:28621 denotes triacetoxyborohydride
T27845 358-365 CHEBI:60004;CHEBI:60004 denotes mixture
T73639 421-428 CHEBI:15377;CHEBI:15377 denotes aqueous
T71101 429-435 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T96786 449-456 CHEBI:15377;CHEBI:15377 denotes aqueous
T30010 567-573 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T67189 662-668 CHEBI:30563;CHEBI:30563 denotes silica
T22030 695-699 CHEBI:32145;CHEBI:32145 denotes MeOH
T49057 760-764 CHEBI:32145;CHEBI:32145 denotes MeOH
T81566 793-798 CHEBI:30808;CHEBI:30808 denotes CDCl3
T29671 1324-1327 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
759 62-65 Chemical denotes DCM
760 83-91 Chemical denotes aldehyde MESH:D000447
761 137-140 Chemical denotes DCM
762 152-163 Chemical denotes acetic acid MESH:D019342
763 245-250 Chemical denotes argon MESH:D001128
764 252-280 Chemical denotes sodium triacetoxyborohydride
765 304-306 Chemical denotes eq
766 383-386 Chemical denotes DCM
767 429-435 Chemical denotes NaHCO3 MESH:D017693
768 482-485 Chemical denotes DCM
769 549-554 Chemical denotes brine MESH:C017082
770 567-573 Chemical denotes Na2SO4
771 662-672 Chemical denotes silica gel MESH:D058428
772 695-699 Chemical denotes MeOH
773 703-706 Chemical denotes DCM
774 760-764 Chemical denotes MeOH
775 765-768 Chemical denotes DCM
776 1638-1653 Chemical denotes C52H87N12O13Si2
777 1611-1615 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T301 3-4 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T302 515-522 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T303 515-522 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T304 716-718 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T305 724-730 http://purl.obolibrary.org/obo/CLO_0007701 denotes mg, 93
T306 736-737 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T307 1655-1658 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T764 5-13 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T765 62-65 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T766 83-91 Chemical denotes aldehyde http://purl.obolibrary.org/obo/CHEBI_17478
T767 137-140 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T768 152-163 Chemical denotes acetic acid http://purl.obolibrary.org/obo/CHEBI_15366
T769 159-163 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T770 245-250 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T771 252-258 Chemical denotes sodium http://purl.obolibrary.org/obo/CHEBI_26708
T772 358-365 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T773 383-386 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T774 429-435 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T775 482-485 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T776 567-573 Chemical denotes Na2SO4 http://purl.obolibrary.org/obo/CHEBI_32149
T777 662-668 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T778 695-699 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T779 703-706 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T780 751-753 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T781 760-764 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T782 765-768 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T783 776-778 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T784 793-798 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T785 811-813 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T786 825-827 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T787 839-841 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T788 853-855 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T789 879-881 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T790 905-907 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T791 958-960 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T792 996-998 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T793 1035-1037 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T794 1054-1056 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T795 1093-1095 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T796 1133-1135 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T797 1209-1211 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T798 1228-1230 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T799 1342-1347 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T12 62-65 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T13 137-140 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T14 383-386 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T15 482-485 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T16 703-706 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T17 765-768 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T312 0-192 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 193-318 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 319-444 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 445-604 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 605-750 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 751-775 Sentence denotes Rf 0.71 (MeOH/DCM 5:95).
T318 776-1323 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 1324-1610 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 1611-1661 Sentence denotes HRMS (ESI+): m/z calcd for C52H87N12O13Si2 [M+H]+:
T321 1662-1679 Sentence denotes 1143.6049, found:
T322 1680-1690 Sentence denotes 1143.6043.