Technology Process of (1S,5R)-3,3,7,9,9-pentamethyl-5-<(phenylmethoxy)methyl>-2,4-dioxaspiro<4.4>non-6-ene
There total 9 articles about (1S,5R)-3,3,7,9,9-pentamethyl-5-<(phenylmethoxy)methyl>-2,4-dioxaspiro<4.4>non-6-ene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
potassium hexamethylsilazane;
In
diethyl ether;
at -78 - 20 ℃;
DOI:10.1021/jo960973a
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 1.) DMSO, oxalyl chloride, 2.) Et3N / CH2Cl2 / 1.) -78 deg C, 2.) warm to room temperature
2: 4.9 g / tetrahydrofuran / 4 h
3: PCC, 4A MS, NaOAc / CH2Cl2 / 5 h
4: 81 percent / NaH / 1,2-dimethoxy-ethane; paraffin / 4 h / 80 °C
5: 92 percent / CuBr*Me2S / tetrahydrofuran / 3 h / 0 °C
6: 86 percent / n-BuLi, diisopropylamine / hexane; tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) -78 deg C, 10 min, 3.) -78 deg to room temperature, 18 h
7: NaN(TMS)2 / toluene / 18 h / Ambient temperature
With
n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; sodium acetate; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; pyridinium chlorochromate;
In
tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; toluene; paraffin;
DOI:10.1021/jo00125a050
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 4.9 g / tetrahydrofuran / 4 h
2: PCC, 4A MS, NaOAc / CH2Cl2 / 5 h
3: 81 percent / NaH / 1,2-dimethoxy-ethane; paraffin / 4 h / 80 °C
4: 92 percent / CuBr*Me2S / tetrahydrofuran / 3 h / 0 °C
5: 86 percent / n-BuLi, diisopropylamine / hexane; tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) -78 deg C, 10 min, 3.) -78 deg to room temperature, 18 h
6: NaN(TMS)2 / toluene / 18 h / Ambient temperature
With
n-butyllithium; copper(I) bromide dimethylsulfide complex; sodium acetate; sodium hexamethyldisilazane; sodium hydride; diisopropylamine; pyridinium chlorochromate;
In
tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; toluene; paraffin;
DOI:10.1021/jo00125a050
![(4S,5S)-4-Benzyloxymethyl-5-((E)-4-chloro-1,1,3-trimethyl-but-3-enyl)-2,2-dimethyl-[1,3]dioxolane](/Databaselist/images/loading.webp)
