Technology Process of [(5E,7E,10E)-(2S,13S,14R)-13-(1-Ethoxy-ethoxy)-2,8,10,14-tetramethyl-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester
There total 20 articles about [(5E,7E,10E)-(2S,13S,14R)-13-(1-Ethoxy-ethoxy)-2,8,10,14-tetramethyl-15-oxo-pentadeca-5,7,10-trienyl]-(4-methoxy-benzyl)-carbamic acid 2-trimethylsilanyl-ethyl ester 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:
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 98 percent / KCN / ethanol
2.1: 99 percent / dimethylformamide
3.1: 88 percent / I2 / Cp2ZrCl2 / CH2Cl2
4.1: 99 percent / TBAF / tetrahydrofuran
5.1: tetrahydrofuran
5.2: 52 percent / NaOEt / Pd(PPh3)4 / ethanol; benzene / Heating
6.1: Dess-Martin reagent / CH2Cl2
7.1: 58 percent / Bun2BOTf; Et3N / CH2Cl2
8.1: 85 percent / PPTS
9.1: 72 percent / LiBH4 / methanol; tetrahydrofuran
10.1: Dess-Martin reagent / CH2Cl2
With
potassium cyanide; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine;
zirconocene dichloride;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
1.1: Deacetylation / 2.1: Etherification / 3.1: Addition / 4.1: Hydrolysis / 5.1: Addition / 5.2: Addition / 6.1: Dess-Martin oxidation / 7.1: Evans aldol reaction / 8.1: Etherification / 9.1: Reduction / 10.1: Oxidation;
DOI:10.7164/antibiotics.51.688
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 99 percent / dimethylformamide
2.1: 88 percent / I2 / Cp2ZrCl2 / CH2Cl2
3.1: 99 percent / TBAF / tetrahydrofuran
4.1: tetrahydrofuran
4.2: 52 percent / NaOEt / Pd(PPh3)4 / ethanol; benzene / Heating
5.1: Dess-Martin reagent / CH2Cl2
6.1: 58 percent / Bun2BOTf; Et3N / CH2Cl2
7.1: 85 percent / PPTS
8.1: 72 percent / LiBH4 / methanol; tetrahydrofuran
9.1: Dess-Martin reagent / CH2Cl2
With
lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine;
zirconocene dichloride;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
1.1: Etherification / 2.1: Addition / 3.1: Hydrolysis / 4.1: Addition / 4.2: Addition / 5.1: Dess-Martin oxidation / 6.1: Evans aldol reaction / 7.1: Etherification / 8.1: Reduction / 9.1: Oxidation;
DOI:10.7164/antibiotics.51.688
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 47 percent HBr
2.1: 79 percent / dimethylformamide
3.1: 98 percent / KCN / ethanol
4.1: 99 percent / dimethylformamide
5.1: 88 percent / I2 / Cp2ZrCl2 / CH2Cl2
6.1: 99 percent / TBAF / tetrahydrofuran
7.1: tetrahydrofuran
7.2: 52 percent / NaOEt / Pd(PPh3)4 / ethanol; benzene / Heating
8.1: Dess-Martin reagent / CH2Cl2
9.1: 58 percent / Bun2BOTf; Et3N / CH2Cl2
10.1: 85 percent / PPTS
11.1: 72 percent / LiBH4 / methanol; tetrahydrofuran
12.1: Dess-Martin reagent / CH2Cl2
With
potassium cyanide; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen bromide; iodine; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine;
zirconocene dichloride;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
1.1: Addition / 2.1: Acylation / 3.1: Deacetylation / 4.1: Etherification / 5.1: Addition / 6.1: Hydrolysis / 7.1: Addition / 7.2: Addition / 8.1: Dess-Martin oxidation / 9.1: Evans aldol reaction / 10.1: Etherification / 11.1: Reduction / 12.1: Oxidation;
DOI:10.7164/antibiotics.51.688
