Technology Process of (E)-(1S,3R,11S,14S,15R,16S)-3-Benzenesulfonyl-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-diene-2,5,18-trione
There total 13 articles about (E)-(1S,3R,11S,14S,15R,16S)-3-Benzenesulfonyl-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-diene-2,5,18-trione which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
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![(E)-(1S,3R,11S,14S,15R,16S)-3-Benzenesulfonyl-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.0<sup>1,15</sup>]octadeca-9,12-diene-2,5,18-trione](/Databaselist/images/loading.webp)
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123206-01-9
(E)-(1S,3R,11S,14S,15R,16S)-3-Benzenesulfonyl-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-diene-2,5,18-trione
- Guidance literature:
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Multi-step reaction with 11 steps
1: 40 percent / BHT / xylene / 130 °C
2: 1.) KOH / 1.) H2O, CH3OH, C6H6, room temp., 2.) ether, CH3OH
3: 100 percent / COCl2, (C2H5)3N, DMSO / CH2Cl2 / -78 °C
4: 58 percent / tetrahydrofuran / -78 °C
5: 1.) n-C4H9Li / 1.) THF, HMPA, 0 deg C
6: 68 percent / PPTS / Ambient temperature
8: 1.) n-C4H9Li, DIBAL-H, 2.) PCC / 1.) THF, O deg C, 2.) CH2Cl2, room temp.
9: 2.) pyridine / 1.) THF, ether, -78 deg C, 2.) 0 deg C
10: 49 percent / 10percent (Ph3P)4Pd, 10percent dppp / tetrahydrofuran / 1.) room temp., 2.) reflux
11: PPTS / tetrahydrofuran; H2O / Heating
With
pyridine; potassium hydroxide; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate;
tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane;
In
tetrahydrofuran; dichloromethane; water; xylene;
DOI:10.1021/ja00203a042
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123206-01-9
(E)-(1S,3R,11S,14S,15R,16S)-3-Benzenesulfonyl-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-diene-2,5,18-trione
- Guidance literature:
-
Multi-step reaction with 12 steps
2: 40 percent / BHT / xylene / 130 °C
3: 1.) KOH / 1.) H2O, CH3OH, C6H6, room temp., 2.) ether, CH3OH
4: 100 percent / COCl2, (C2H5)3N, DMSO / CH2Cl2 / -78 °C
5: 58 percent / tetrahydrofuran / -78 °C
6: 1.) n-C4H9Li / 1.) THF, HMPA, 0 deg C
7: 68 percent / PPTS / Ambient temperature
9: 1.) n-C4H9Li, DIBAL-H, 2.) PCC / 1.) THF, O deg C, 2.) CH2Cl2, room temp.
10: 2.) pyridine / 1.) THF, ether, -78 deg C, 2.) 0 deg C
11: 49 percent / 10percent (Ph3P)4Pd, 10percent dppp / tetrahydrofuran / 1.) room temp., 2.) reflux
12: PPTS / tetrahydrofuran; H2O / Heating
With
pyridine; potassium hydroxide; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate;
tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane;
In
tetrahydrofuran; dichloromethane; water; xylene;
DOI:10.1021/ja00203a042
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123206-01-9
(E)-(1S,3R,11S,14S,15R,16S)-3-Benzenesulfonyl-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-diene-2,5,18-trione
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 100 percent / COCl2, (C2H5)3N, DMSO / CH2Cl2 / -78 °C
2: 58 percent / tetrahydrofuran / -78 °C
3: 1.) n-C4H9Li / 1.) THF, HMPA, 0 deg C
4: 68 percent / PPTS / Ambient temperature
6: 1.) n-C4H9Li, DIBAL-H, 2.) PCC / 1.) THF, O deg C, 2.) CH2Cl2, room temp.
7: 2.) pyridine / 1.) THF, ether, -78 deg C, 2.) 0 deg C
8: 49 percent / 10percent (Ph3P)4Pd, 10percent dppp / tetrahydrofuran / 1.) room temp., 2.) reflux
9: PPTS / tetrahydrofuran; H2O / Heating
With
pyridine; n-butyllithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate;
tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane;
In
tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ja00203a042
