Technology Process of (4aR,5R,8aS)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-8a-methyl-octahydro-naphthalen-1-one
There total 12 articles about (4aR,5R,8aS)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-8a-methyl-octahydro-naphthalen-1-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(4R,4aR,8aS)-4-(tert-Butyl-diphenyl-silanyloxy)-8a-methyl-8-trimethylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene;
With
3-chloro-benzenecarboperoxoic acid;
In
pentane;
at 0 ℃;
for 0.416667h;
With
hydrogenchloride;
In
methanol;
at 0 ℃;
for 0.0833333h;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 4.53 g / p-TsOH / acetic acid / 5 h / 20 °C
2.1: 5.33 g / p-TsOH / toluene / 12 h / Heating; Dean-Stark apparatus
3.1: Na; liq. NH3 / 1 h
4.1: BH3*THF / 15 h / 0 - 20 °C
4.2: 83 percent / NaOH (3N); H2O2 (30 percent) / tetrahydrofuran / 4 h
5.1: 96 percent / mol. sieves; NMO; TPAP / CH2Cl2 / 3 h / 20 °C
6.1: 85 percent / NaOMe / methanol / 24 h / 20 °C
7.1: Li; liq. NH3 / methanol / 2 h / -78 °C
8.1: p-TsOH; H2O; Me2CO / 10 h / 20 °C
9.1: 98 percent / imidazole / dimethylformamide / 48 h / 20 °C
10.1: Et3N; NaI / acetonitrile / 12 h / 20 °C
11.1: mCPBA (70 percent) / pentane / 0.42 h / 0 °C
11.2: HCl (12N) / methanol / 0.08 h / 0 °C
With
1H-imidazole; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; borane-THF; ammonia; water; sodium methylate; sodium; lithium; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; acetone; sodium iodide;
In
methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; pentane;
1.1: Cyclization / 2.1: Etherification / 3.1: Reduction / 4.1: Addition / 4.2: Oxidation / 5.1: Oxidation / 6.1: Isomerization / 7.1: Reduction / 8.1: Hydrolysis / 9.1: Substitution / 10.1: Substitution / 11.1: Oxidation / 11.2: Hydrolysis;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 5.33 g / p-TsOH / toluene / 12 h / Heating; Dean-Stark apparatus
2.1: Na; liq. NH3 / 1 h
3.1: BH3*THF / 15 h / 0 - 20 °C
3.2: 83 percent / NaOH (3N); H2O2 (30 percent) / tetrahydrofuran / 4 h
4.1: 96 percent / mol. sieves; NMO; TPAP / CH2Cl2 / 3 h / 20 °C
5.1: 85 percent / NaOMe / methanol / 24 h / 20 °C
6.1: Li; liq. NH3 / methanol / 2 h / -78 °C
7.1: p-TsOH; H2O; Me2CO / 10 h / 20 °C
8.1: 98 percent / imidazole / dimethylformamide / 48 h / 20 °C
9.1: Et3N; NaI / acetonitrile / 12 h / 20 °C
10.1: mCPBA (70 percent) / pentane / 0.42 h / 0 °C
10.2: HCl (12N) / methanol / 0.08 h / 0 °C
With
1H-imidazole; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; borane-THF; ammonia; water; sodium methylate; sodium; lithium; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; acetone; sodium iodide;
In
methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; pentane;
1.1: Etherification / 2.1: Reduction / 3.1: Addition / 3.2: Oxidation / 4.1: Oxidation / 5.1: Isomerization / 6.1: Reduction / 7.1: Hydrolysis / 8.1: Substitution / 9.1: Substitution / 10.1: Oxidation / 10.2: Hydrolysis;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o
