Technology Process of (E)-(3S,4S,7S,8R)-1,8-Bis-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undec-9-en-5-one
There total 13 articles about (E)-(3S,4S,7S,8R)-1,8-Bis-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undec-9-en-5-one 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:
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Multi-step reaction with 9 steps
1: 85 percent / di-n-butylboron triflate, Et3N / CH2Cl2 / -78 deg C up to RT
2: 85 percent / NaOMe / methanol; CH2Cl2 / 0.17 h / -15 °C
3: 88 percent / DIBAL-H / CH2Cl2 / -78 - -15 °C
4: 82 percent / Bu3P / dimethylformamide / Ambient temperature
5: 96 percent / imidazole / dimethylformamide / 85 °C
6: 99 percent / O3 / tetrahydrofuran; methanol; H2O / Ambient temperature
7: 64 percent / 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C up to RT
8: 92 percent / 1.) (CF3CO)2O/Me2SO; 2.) Et3N / CH2Cl2 / 1.) -78 deg C; 2.) up to RT
9: 82 percent / Bu3SnH, AIBN / toluene / Heating
With
1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); tributylphosphine; di-n-butylboryl trifluoromethanesulfonate; tri-n-butyl-tin hydride; sodium methylate; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)73993-1
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 84 percent / TsOH / dimethylformamide / 55 °C
2: 78 percent / DIBAL-H / CH2Cl2; toluene / -78 deg C up to RT
3: 83 percent / Me2SO, (COCl)2, Et3N / CH2Cl2 / -78 deg C up to RT
4: 64 percent / 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C up to RT
5: 92 percent / 1.) (CF3CO)2O/Me2SO; 2.) Et3N / CH2Cl2 / 1.) -78 deg C; 2.) up to RT
6: 82 percent / Bu3SnH, AIBN / toluene / Heating
With
n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)73993-1
