JP2020055786A5 - - Google Patents
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- Publication number
- JP2020055786A5 JP2020055786A5 JP2018188693A JP2018188693A JP2020055786A5 JP 2020055786 A5 JP2020055786 A5 JP 2020055786A5 JP 2018188693 A JP2018188693 A JP 2018188693A JP 2018188693 A JP2018188693 A JP 2018188693A JP 2020055786 A5 JP2020055786 A5 JP 2020055786A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl acetate
- mmol
- toluene
- nmr
- mannopyranosyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- 0 C[C@]1[C@@](*)C[C@@](*)OC1COCc1ccccc1 Chemical compound C[C@]1[C@@](*)C[C@@](*)OC1COCc1ccccc1 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- -1 Methoxyphenyl Chemical group 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- POSGKEMZIOOTLQ-YLOHMFRLSA-N 2-[(3R,4R,5S,6R)-2-benzyl-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]isoindole-1,3-dione Chemical compound OC[C@H]1OC(O)(Cc2ccccc2)[C@@H]([C@@H](O)[C@@H]1O)N1C(=O)c2ccccc2C1=O POSGKEMZIOOTLQ-YLOHMFRLSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 240000000385 Brassica napus var. napus Species 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- SLJMUUMZMKOUDI-YLOHMFRLSA-N C(C1=CC=CC=C1)C1([C@@H]([C@@H](O)[C@H](O)[C@H](O1)CO)N1C(C=2C(C1=O)=CC=CC=2)=O)F Chemical compound C(C1=CC=CC=C1)C1([C@@H]([C@@H](O)[C@H](O)[C@H](O1)CO)N1C(C=2C(C1=O)=CC=CC=2)=O)F SLJMUUMZMKOUDI-YLOHMFRLSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910000175 cerite Inorganic materials 0.000 description 1
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Substances CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000937 glycosyl acceptor Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018188693A JP7198482B2 (ja) | 2018-10-03 | 2018-10-03 | 糖化合物、糖化合物の製造方法、ＥＮＧａｓｅ活性検出用組成物、新規ＥＮＧａｓｅのスクリーニング方法、及びＥＮＧａｓｅ活性阻害剤のスクリーニング方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018188693A JP7198482B2 (ja) | 2018-10-03 | 2018-10-03 | 糖化合物、糖化合物の製造方法、ＥＮＧａｓｅ活性検出用組成物、新規ＥＮＧａｓｅのスクリーニング方法、及びＥＮＧａｓｅ活性阻害剤のスクリーニング方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020055786A JP2020055786A (ja) | 2020-04-09 |
| JP2020055786A5 true JP2020055786A5 (https=) | 2021-11-11 |
| JP7198482B2 JP7198482B2 (ja) | 2023-01-04 |
Family
ID=70106391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018188693A Active JP7198482B2 (ja) | 2018-10-03 | 2018-10-03 | 糖化合物、糖化合物の製造方法、ＥＮＧａｓｅ活性検出用組成物、新規ＥＮＧａｓｅのスクリーニング方法、及びＥＮＧａｓｅ活性阻害剤のスクリーニング方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP7198482B2 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114835834B (zh) * | 2022-05-16 | 2023-03-10 | 井冈山大学 | 一种改性环状低聚物及其制备方法、一种微纳纤维膜及其应用 |
| WO2025198057A1 (ja) * | 2024-03-22 | 2025-09-25 | 国立大学法人群馬大学 | 抗体上糖鎖に作用するＥＮＧａｓｅの探索プローブ |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6798085B2 (ja) | 2016-06-14 | 2020-12-09 | 国立大学法人群馬大学 | 糖化合物、糖化合物の製造方法、ＥＮＧａｓｅ活性検出用組成物、及びＥＮＧａｓｅ活性阻害剤のスクリーニング方法 |
-
2018
- 2018-10-03 JP JP2018188693A patent/JP7198482B2/ja active Active
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