Technology Process of (R)-Methoxy-phenyl-acetic acid (S)-2-{3-benzyloxy-2-propoxy-5-[(2S,5S)-5-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan-2-yl]-benzenesulfonyl}-1-methyl-ethyl ester
There total 11 articles about (R)-Methoxy-phenyl-acetic acid (S)-2-{3-benzyloxy-2-propoxy-5-[(2S,5S)-5-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan-2-yl]-benzenesulfonyl}-1-methyl-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 9 steps
1: 1.3 kg / bromine, sodium acetate / acetic acid / 45 h
2: 76 percent / copper / pyridine / 16 h / 95 °C
3: 1.04 kg / K2CO3 / dimethylformamide / 75 °C
4: 1.45 kg / 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (ETB), triethylamine / 2 h / 90 °C
5: 65 percent / 3-chloroperbenzoic acid / CH2Cl2 / 2 h / Ambient temperature
6: 73 percent / lithium aluminium hydride, (S)-(-)-binaphthol / ethanol; tetrahydrofuran / 1.5 h
7: 55 percent / NaBH4 / CH2Cl2; ethanol / 1 h / Ambient temperature
8: 75 percent / LDA / cyclohexane; tetrahydrofuran / 0.17 h / -70 °C
9: 4-(dimethylamino)pyridine, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 3 h
With
dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; bromine; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium acetate; copper; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide;
In
tetrahydrofuran; pyridine; ethanol; dichloromethane; cyclohexane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jm00097a005
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 76 percent / copper / pyridine / 16 h / 95 °C
2: 1.04 kg / K2CO3 / dimethylformamide / 75 °C
3: 1.45 kg / 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (ETB), triethylamine / 2 h / 90 °C
4: 65 percent / 3-chloroperbenzoic acid / CH2Cl2 / 2 h / Ambient temperature
5: 73 percent / lithium aluminium hydride, (S)-(-)-binaphthol / ethanol; tetrahydrofuran / 1.5 h
6: 55 percent / NaBH4 / CH2Cl2; ethanol / 1 h / Ambient temperature
7: 75 percent / LDA / cyclohexane; tetrahydrofuran / 0.17 h / -70 °C
8: 4-(dimethylamino)pyridine, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 3 h
With
dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; (S)-[1,1']-binaphthalenyl-2,2'-diol; copper; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide;
In
tetrahydrofuran; pyridine; ethanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1021/jm00097a005
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 1.45 kg / 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (ETB), triethylamine / 2 h / 90 °C
2: 65 percent / 3-chloroperbenzoic acid / CH2Cl2 / 2 h / Ambient temperature
3: 73 percent / lithium aluminium hydride, (S)-(-)-binaphthol / ethanol; tetrahydrofuran / 1.5 h
4: 55 percent / NaBH4 / CH2Cl2; ethanol / 1 h / Ambient temperature
5: 75 percent / LDA / cyclohexane; tetrahydrofuran / 0.17 h / -70 °C
6: 4-(dimethylamino)pyridine, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 3 h
With
dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; (S)-[1,1']-binaphthalenyl-2,2'-diol; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide;
In
tetrahydrofuran; ethanol; dichloromethane; cyclohexane;
DOI:10.1021/jm00097a005
