Technology Process of (1R,4aS,5S,6S,8S,8aR)-5-Benzyloxy-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde
There total 12 articles about (1R,4aS,5S,6S,8S,8aR)-5-Benzyloxy-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde 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:
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107173-18-2
(1R,4aS,5S,6S,8S,8aR)-5-Benzyloxy-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde
- Guidance literature:
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With
BTH;
In
toluene;
at 155 ℃;
for 24h;
DOI:10.1021/jo00383a012
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107173-18-2
(1R,4aS,5S,6S,8S,8aR)-5-Benzyloxy-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde
- Guidance literature:
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Multi-step reaction with 9 steps
1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, -78 deg C, 1.5 h
2: 79 percent / Red-Al / diethyl ether / 1 h / Ambient temperature
3: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, HMPA, -78 deg C, 5 min
4: 99 percent / tetrabutylammonium fluoride / hexane / 6 h / Ambient temperature
5: 82 percent / oxalyl chloride, Me2SO, Et3N / CH2Cl2 / 30 h / -78 °C
6: 97 percent / CH2Cl2 / 72 h / Ambient temperature
7: 100 percent / DIBAH / diethyl ether; hexane / 0.58 h / -78 °C
8: 89 percent / oxylal chloride, Me2SO / CH2Cl2 / 0.5 h / -78 °C
9: 93 percent / BTH / toluene / 24 h / 155 °C
With
n-butyllithium; 1,10-Phenanthroline; oxalyl dichloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/jo00383a012
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107173-18-2
(1R,4aS,5S,6S,8S,8aR)-5-Benzyloxy-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 91 percent / oxalyl chloride, Me2SO / CH2Cl2 / 0.75 h / -78 °C
2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, -78 deg C, 1.5 h
3: 79 percent / Red-Al / diethyl ether / 1 h / Ambient temperature
4: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, HMPA, -78 deg C, 5 min
5: 99 percent / tetrabutylammonium fluoride / hexane / 6 h / Ambient temperature
6: 82 percent / oxalyl chloride, Me2SO, Et3N / CH2Cl2 / 30 h / -78 °C
7: 97 percent / CH2Cl2 / 72 h / Ambient temperature
8: 100 percent / DIBAH / diethyl ether; hexane / 0.58 h / -78 °C
9: 89 percent / oxylal chloride, Me2SO / CH2Cl2 / 0.5 h / -78 °C
10: 93 percent / BTH / toluene / 24 h / 155 °C
With
n-butyllithium; 1,10-Phenanthroline; oxalyl dichloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/jo00383a012
