Technology Process of (7E,12E)-(2R,3S,10S,15R)-16-Benzyloxy-2,10-dihydroxy-3,13,15-trimethyl-hexadeca-7,12-dien-6-one
There total 33 articles about (7E,12E)-(2R,3S,10S,15R)-16-Benzyloxy-2,10-dihydroxy-3,13,15-trimethyl-hexadeca-7,12-dien-6-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 78 percent / triphenylphosphine, diethyl azodicarboxylate / toluene; benzene / 1.) - 30 deg C to room temperature, 2 h, 2.) room temperature, 2 h
2: 90 percent / KOH / tetrahydrofuran; H2O; methanol / 16 h / Ambient temperature
3: 82 percent / imidazole / CH2Cl2 / 16 h / Ambient temperature
4: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, MeOH, -70 deg C, 2.) -60 to -40 deg C
5: pyridine / CH2Cl2 / 24 h / Ambient temperature
6: NaI / acetone / 1.5 h / Heating
7: 1.) n-BuLi / 1.) hexane, THF, -25 deg C, 1.25 h, 2.) THF, -25 deg C, 2.5 h
8: 1.) t-BuLi, 3.) HMPA
9: TBAF / tetrahydrofuran / 90 h / Ambient temperature
10: TsOH, I2 / tetrahydrofuran / Ambient temperature
With
pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; toluene-4-sulfonic acid; ozone; triphenylphosphine; sodium iodide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; benzene;
DOI:10.1016/S0040-4020(01)85578-2
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 82 percent / imidazole / CH2Cl2 / 16 h / Ambient temperature
2: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, MeOH, -70 deg C, 2.) -60 to -40 deg C
3: pyridine / CH2Cl2 / 24 h / Ambient temperature
4: NaI / acetone / 1.5 h / Heating
5: 1.) n-BuLi / 1.) hexane, THF, -25 deg C, 1.25 h, 2.) THF, -25 deg C, 2.5 h
6: 1.) t-BuLi, 3.) HMPA
7: TBAF / tetrahydrofuran / 90 h / Ambient temperature
8: TsOH, I2 / tetrahydrofuran / Ambient temperature
With
pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; toluene-4-sulfonic acid; ozone; sodium iodide;
In
tetrahydrofuran; dichloromethane; acetone;
DOI:10.1016/S0040-4020(01)85578-2
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 89 percent / pyridine / CH2Cl2 / 1.) 15 min, cooling, 2.) 24 h, room temperature
2: 72 percent / HMPA / tetrahydrofuran / 1.) 30 min, cooling, 2.) 9 h, room temperature
4: 80 percent / NaH, HMPA / tetrahydrofuran / 1.) 45 min, 0 deg C, 2.) room temperature, 18 h
5: 1.) t-BuLi, 3.) HMPA
6: TBAF / tetrahydrofuran / 90 h / Ambient temperature
7: TsOH, I2 / tetrahydrofuran / Ambient temperature
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; sodium hydride; toluene-4-sulfonic acid;
In
tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)85578-2