Technology Process of (5S,6S,11S,E)-methyl 12-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,11-dimethyldodec-2-enoate
There total 14 articles about (5S,6S,11S,E)-methyl 12-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,11-dimethyldodec-2-enoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.42 h / 0 °C / Inert atmosphere
1.2: 2 h / -78 °C / Inert atmosphere
2.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C
3.1: lithium borohydride / methanol / 0.5 h / 0 °C / Inert atmosphere
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
5.2: 6 h / -78 - 20 °C
6.1: cyclohexene; dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 20 °C
6.2: 3 h / 0 - 20 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C
8.1: benzene / 2 h / Reflux
9.1: pyridinium p-toluenesulfonate / methanol / 12 h / 0 - 20 °C
With
2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; dimethylsulfide borane complex; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; titanium tetrachloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; cyclohexene;
In
tetrahydrofuran; methanol; dichloromethane; benzene;
1.2: |Evans Aldol Reaction / 4.1: |Swern Oxidation / 4.2: |Swern Oxidation / 5.1: |Julia Olefin Synthesis / 5.2: |Julia Olefin Synthesis / 7.1: |Swern Oxidation / 7.2: |Swern Oxidation / 8.1: |Wittig Olefination;
DOI:10.1016/j.tet.2012.11.075
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
1.2: 6 h / -78 - 20 °C
2.1: cyclohexene; dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 20 °C
2.2: 3 h / 0 - 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C
4.1: benzene / 2 h / Reflux
5.1: pyridinium p-toluenesulfonate / methanol / 12 h / 0 - 20 °C
With
oxalyl dichloride; dimethylsulfide borane complex; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; dimethyl sulfoxide; cyclohexene;
In
tetrahydrofuran; methanol; dichloromethane; benzene;
1.1: |Julia Olefin Synthesis / 1.2: |Julia Olefin Synthesis / 3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 4.1: |Wittig Olefination;
DOI:10.1016/j.tet.2012.11.075
