Technology Process of (S)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-3-hydroxy-propionic acid ethyl ester
There total 19 articles about (S)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-3-hydroxy-propionic acid 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 12 steps
2: ozone / -78 °C
3: NaBH4 / ethanol / 0.5 h / 0 °C
4: PBr3, LiBr, collidine / diethyl ether; tetrahydrofuran
5: nitromethane
6: t-BuLi / tetrahydrofuran; dimethylformamide / -63 °C
7: 78 percent / tetrahydrofuran / -63 deg C -> room temperature
8: H2O, AcOH / tetrahydrofuran / 48 h / -10 °C
9: 1.) NaBH4, 2.) KOH, EtOH / 1.) MeOH, 0 deg C, 15 min, 2.) reflux, 22 h
10: 70 percent / t-BuOOH, Ti(O-i-Pr)4 / CH2Cl2 / 1.5 h / -20 °C
11: aldol reaction
12: tetrahydrofuran / 0.5 h / -78 °C
With
titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; potassium hydroxide; sodium tetrahydroborate; ethanol; water; tert.-butyl lithium; phosphorus tribromide; ozone; acetic acid; lithium bromide;
In
tetrahydrofuran; diethyl ether; nitromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00382a065
- Guidance literature:
-
Multi-step reaction with 10 steps
1: NaBH4 / ethanol / 0.5 h / 0 °C
2: PBr3, LiBr, collidine / diethyl ether; tetrahydrofuran
3: nitromethane
4: t-BuLi / tetrahydrofuran; dimethylformamide / -63 °C
5: 78 percent / tetrahydrofuran / -63 deg C -> room temperature
6: H2O, AcOH / tetrahydrofuran / 48 h / -10 °C
7: 1.) NaBH4, 2.) KOH, EtOH / 1.) MeOH, 0 deg C, 15 min, 2.) reflux, 22 h
8: 70 percent / t-BuOOH, Ti(O-i-Pr)4 / CH2Cl2 / 1.5 h / -20 °C
9: aldol reaction
10: tetrahydrofuran / 0.5 h / -78 °C
With
titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; potassium hydroxide; sodium tetrahydroborate; ethanol; water; tert.-butyl lithium; phosphorus tribromide; acetic acid; lithium bromide;
In
tetrahydrofuran; diethyl ether; nitromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00382a065
- Guidance literature:
-
Multi-step reaction with 9 steps
1: PBr3, LiBr, collidine / diethyl ether; tetrahydrofuran
2: nitromethane
3: t-BuLi / tetrahydrofuran; dimethylformamide / -63 °C
4: 78 percent / tetrahydrofuran / -63 deg C -> room temperature
5: H2O, AcOH / tetrahydrofuran / 48 h / -10 °C
6: 1.) NaBH4, 2.) KOH, EtOH / 1.) MeOH, 0 deg C, 15 min, 2.) reflux, 22 h
7: 70 percent / t-BuOOH, Ti(O-i-Pr)4 / CH2Cl2 / 1.5 h / -20 °C
8: aldol reaction
9: tetrahydrofuran / 0.5 h / -78 °C
With
titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; potassium hydroxide; sodium tetrahydroborate; ethanol; water; tert.-butyl lithium; phosphorus tribromide; acetic acid; lithium bromide;
In
tetrahydrofuran; diethyl ether; nitromethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00382a065
