Technology Process of (2R,3R,7E)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol
There total 24 articles about (2R,3R,7E)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol 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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378198-08-4
(2R,3R,7E)-2-(tert-butyldimethylsiliyloxy)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonene
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378198-09-5
(2R,3R,7E)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol
- Guidance literature:
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With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
for 48h;
Heating;
DOI:10.1021/jo010154c
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378198-09-5
(2R,3R,7E)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol
- Guidance literature:
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Multi-step reaction with 14 steps
1.1: 99 percent / imidazole / dimethylformamide / 1 h / 20 °C
2.1: SOCl2; 4-DMAP / pyridine / -50 - 0 °C
2.2: 62 percent / SeO2; salicylic acid; tBuOOH / CH2Cl2 / 48 h / 20 °C
3.1: 17 percent / H2 / Pd/C / ethanol / 12 h / 20 °C / 760.05 Torr
4.1: 98 percent / TBAF / tetrahydrofuran / 1 h / Heating
5.1: 96 percent / Et3N; SO3*Py / dimethylsulfoxide / 1 h / 20 °C
6.1: 87 percent / Bu2BOTf; Et3N / CH2Cl2 / -78 - 0 °C
7.1: 98 percent / AlMe3 / toluene; CH2Cl2 / 24 h / 0 - 20 °C
8.1: 98 percent / 2,6-lutidine / CH2Cl2 / -78 - -10 °C
9.1: 99 percent / DIBALH / tetrahydrofuran / 0.5 h / -78 °C
10.1: 70 percent / NaH / tetrahydrofuran / 2 h / 20 °C
11.1: 92 percent / NiCl2*xH2O; NaBH4 / methanol / 3 h / 0 °C
12.1: 76 percent / LDA / tetrahydrofuran / 4 h / -78 - 0 °C
13.1: 198 mg / Na-Hg / methanol / 20 °C
14.1: 93 percent / TBAF / tetrahydrofuran / 48 h / Heating
With
1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; thionyl chloride; sodium amalgam; pyridine-SO3 complex; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; triethylamine; nickel dichloride; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo010154c
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564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5
(3aR)-(+)-sclareolide
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378198-09-5
(2R,3R,7E)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol
- Guidance literature:
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Multi-step reaction with 15 steps
1.1: 100 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C
2.1: 99 percent / imidazole / dimethylformamide / 1 h / 20 °C
3.1: SOCl2; 4-DMAP / pyridine / -50 - 0 °C
3.2: 62 percent / SeO2; salicylic acid; tBuOOH / CH2Cl2 / 48 h / 20 °C
4.1: 17 percent / H2 / Pd/C / ethanol / 12 h / 20 °C / 760.05 Torr
5.1: 98 percent / TBAF / tetrahydrofuran / 1 h / Heating
6.1: 96 percent / Et3N; SO3*Py / dimethylsulfoxide / 1 h / 20 °C
7.1: 87 percent / Bu2BOTf; Et3N / CH2Cl2 / -78 - 0 °C
8.1: 98 percent / AlMe3 / toluene; CH2Cl2 / 24 h / 0 - 20 °C
9.1: 98 percent / 2,6-lutidine / CH2Cl2 / -78 - -10 °C
10.1: 99 percent / DIBALH / tetrahydrofuran / 0.5 h / -78 °C
11.1: 70 percent / NaH / tetrahydrofuran / 2 h / 20 °C
12.1: 92 percent / NiCl2*xH2O; NaBH4 / methanol / 3 h / 0 °C
13.1: 76 percent / LDA / tetrahydrofuran / 4 h / -78 - 0 °C
14.1: 198 mg / Na-Hg / methanol / 20 °C
15.1: 93 percent / TBAF / tetrahydrofuran / 48 h / Heating
With
1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; thionyl chloride; sodium amalgam; pyridine-SO3 complex; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; triethylamine; nickel dichloride; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo010154c