Technology Process of rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one, 2,2-dimethyltrimethylene acetal
There total 9 articles about rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one, 2,2-dimethyltrimethylene acetal which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1: TsOH / benzene
2: n-BuLi, i-Pr2-NH / hexane; tetrahydrofuran / 1h, room temperature then 15min at room temperature
3: 66 percent / 85percent MCPBA, triethylammonium fluoride / CH2Cl2
4: 81 percent / pyridine / Ambient temperature
5: 1.) Li2CO3, 85percent MCPBA, 1,6-di-tert-butyl-4-methylphenol; 2.) 1M NaOH / 1.) dichloromethane, reflux, 36h; 2.) THF, 3d
6: LiAlH4, sodium potassium tartrate / tetrahydrofuran; diethyl ether
7: 1.) pyridine; 2.) pyridine / 1.) dichloromethane, -4 degC, 2d; 2.) room temperature, 36h
With
pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 1,6-di-t-butyl-4-methylphenol; lithium carbonate; Rochelle's salt; toluene-4-sulfonic acid; triethylamine hydrofluoride; diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1016/S0040-4020(01)87331-2
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 66 percent / 85percent MCPBA, triethylammonium fluoride / CH2Cl2
2: 81 percent / pyridine / Ambient temperature
3: 1.) Li2CO3, 85percent MCPBA, 1,6-di-tert-butyl-4-methylphenol; 2.) 1M NaOH / 1.) dichloromethane, reflux, 36h; 2.) THF, 3d
4: LiAlH4, sodium potassium tartrate / tetrahydrofuran; diethyl ether
5: 1.) pyridine; 2.) pyridine / 1.) dichloromethane, -4 degC, 2d; 2.) room temperature, 36h
With
pyridine; sodium hydroxide; lithium aluminium tetrahydride; 1,6-di-t-butyl-4-methylphenol; lithium carbonate; Rochelle's salt; triethylamine hydrofluoride; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(01)87331-2
- Guidance literature:
-
Multi-step reaction with 6 steps
1: n-BuLi, i-Pr2-NH / hexane; tetrahydrofuran / 1h, room temperature then 15min at room temperature
2: 66 percent / 85percent MCPBA, triethylammonium fluoride / CH2Cl2
3: 81 percent / pyridine / Ambient temperature
4: 1.) Li2CO3, 85percent MCPBA, 1,6-di-tert-butyl-4-methylphenol; 2.) 1M NaOH / 1.) dichloromethane, reflux, 36h; 2.) THF, 3d
5: LiAlH4, sodium potassium tartrate / tetrahydrofuran; diethyl ether
6: 1.) pyridine; 2.) pyridine / 1.) dichloromethane, -4 degC, 2d; 2.) room temperature, 36h
With
pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 1,6-di-t-butyl-4-methylphenol; lithium carbonate; Rochelle's salt; triethylamine hydrofluoride; diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1016/S0040-4020(01)87331-2
