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CAS No.: | 253128-41-5 |
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Name: | Eribulin |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C40H59NO11 |
Molecular Weight: | 729.909 |
Synonyms: | B 1939;E 7389;ER 086526;Eribulin; |
EINECS: | 803-583-7 |
Density: | 1.29±0.1 g/cm3(Predicted) |
PSA: | 146.39000 |
LogP: | 4.13830 |
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo [24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 30℃; for 16h; | 89% |
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo [24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
Conditions | Yield |
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Stage #1: C45H67NO13 With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 20℃; for 2.5h; Stage #2: With potassium carbonate In methanol at 20℃; for 2h; | 88% |
With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 20℃; for 5.5h; | 1.6 mg |
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-azido-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylidene)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo [24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
Conditions | Yield |
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With trimethylphosphane In tetrahydrofuran; water at 20℃; for 22h; | 87% |
With water; trimethylphosphane In tetrahydrofuran at 20℃; for 22h; Staudinger Azide Reduction; | 87% |
With triphenylphosphine In tetrahydrofuran; water at 21℃; for 24h; Inert atmosphere; |
C41H60O14S
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo [24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
Conditions | Yield |
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With ammonia In methanol at 20℃; | |
Multi-step reaction with 2 steps 1: tetrabutylammoniun azide / N,N-dimethyl-formamide / 3.5 h / 83 °C 2: trimethylphosphane; water / tetrahydrofuran / 22 h / 20 °C View Scheme |
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-2,3-Dihydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo [24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 90 percent / collidine / CH2Cl2 / 0 °C 2: NH3 / methanol / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: 2,4,6-trimethyl-pyridine; pyridine / dichloromethane / -10 °C / Industrial scale 1.2: 10 - 30 °C / Industrial scale 2.1: ammonium hydroxide / dichloromethane; isopropyl alcohol / 10 - 30 °C / Industrial scale View Scheme | |
Multi-step reaction with 3 steps 1: 2,4,6-trimethyl-pyridine / dichloromethane / 76.67 h / 0 - 4 °C 2: tetrabutylammoniun azide / N,N-dimethyl-formamide / 3.5 h / 83 °C 3: trimethylphosphane; water / tetrahydrofuran / 22 h / 20 °C View Scheme |
ER-809681
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo [24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
Conditions | Yield |
---|---|
With ammonium hydroxide In dichloromethane; isopropyl alcohol at 10 - 30℃; Industrial scale; |
(1R,2S,3S,4S,5S,6RS,11S,14S,17S,19R,21R,23S,25R,26R,27S,31R,34S)-25-[(2S)-2,3-dihydroxypropyl]-2,5-dihydroxy-26-methoxy-19-methyl-13,20-bis(methylene)-24,35,36,37,38,39-hexaoxaheptacyclo[29.3.1.13,6.14,34.111,14.117,21.023,27] nonatriacontane-8,29-dione
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo [24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: pyridinium p-toluenesulfonate / dichloromethane / 10 - 20 °C / Industrial scale 2.1: 2,4,6-trimethyl-pyridine; pyridine / dichloromethane / -10 °C / Industrial scale 2.2: 10 - 30 °C / Industrial scale 3.1: ammonium hydroxide / dichloromethane; isopropyl alcohol / 10 - 30 °C / Industrial scale View Scheme |
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo [24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 h / 20 °C / Inert atmosphere 1.2: Dowex 50WX8-400 resin / 1 h 1.3: 1.5 h / 20 °C 2.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2.5 h / 0 - 20 °C 2.2: 2 h / 20 °C View Scheme |
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo [24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
Conditions | Yield |
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Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C 2: trimethylsilyl trifluoromethanesulfonate; 2,6-dimethylpyridine / dichloromethane / 5.5 h / 0 - 20 °C View Scheme |
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo [24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
Conditions | Yield |
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With ammonium hydroxide In dichloromethane; water; isopropyl alcohol at 10 - 30℃; Solvent; Temperature; |