Technology Process of isopropyl [2R,(1E,3R),3R,(4Z),4R]-7-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}-hept-4-enoate
There total 11 articles about isopropyl [2R,(1E,3R),3R,(4Z),4R]-7-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}-hept-4-enoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(3-(isopropoxycarbonyl)propyl)triphenylphosphonium bromide;
With
potassium hexamethylsilazane;
In
tetrahydrofuran; toluene;
at 0 - 3 ℃;
for 0.666667h;
[2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propionaldehyde;
In
tetrahydrofuran; toluene;
at -70 - 0 ℃;
for 3.5h;
DOI:10.1021/jo048035v
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: imidazole / dimethylformamide / 20 °C
2.1: 103 percent / diisobutylaluminum hydride / toluene / 1.5 h / -60 °C
3.1: 98 percent / triethylamine / tetrahydrofuran / 2 h / 5 - 20 °C
4.1: tert-butyllithium / tetrahydrofuran / 0.67 h / -70 - -60 °C
4.2: litium 2-thienylcyanocuprate / tetrahydrofuran / 0.17 h / -60 °C
4.3: 63 percent / trimethylsilyl bromide / tetrahydrofuran; CH2Cl2 / 2 h / -60 °C
5.1: 9-BBN / tetrahydrofuran / 2.5 h
5.2: 78 percent / H2O2; sodium hydroxide / tetrahydrofuran / 5 - 20 °C
6.1: 92 percent / dimethyl sulfoxide; triethylamine; oxalyl chloride / CH2Cl2 / -60 - 20 °C
7.1: potassium tert-butoxide / tetrahydrofuran / 0.67 h / 3 °C
7.2: 94 percent / tetrahydrofuran / 1 h / -2 °C
8.1: 160 mg / DBU / acetone
With
1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; potassium tert-butylate; tert.-butyl lithium; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
6.1: Swern oxidation;
DOI:10.1021/jo048035v
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 98 percent / triethylamine / tetrahydrofuran / 2 h / 5 - 20 °C
2.1: tert-butyllithium / tetrahydrofuran / 0.67 h / -70 - -60 °C
2.2: litium 2-thienylcyanocuprate / tetrahydrofuran / 0.17 h / -60 °C
2.3: 63 percent / trimethylsilyl bromide / tetrahydrofuran; CH2Cl2 / 2 h / -60 °C
3.1: 9-BBN / tetrahydrofuran / 2.5 h
3.2: 78 percent / H2O2; sodium hydroxide / tetrahydrofuran / 5 - 20 °C
4.1: 92 percent / dimethyl sulfoxide; triethylamine; oxalyl chloride / CH2Cl2 / -60 - 20 °C
5.1: potassium tert-butoxide / tetrahydrofuran / 0.67 h / 3 °C
5.2: 94 percent / tetrahydrofuran / 1 h / -2 °C
6.1: 160 mg / DBU / acetone
With
9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; potassium tert-butylate; tert.-butyl lithium; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
In
tetrahydrofuran; dichloromethane; acetone;
4.1: Swern oxidation;
DOI:10.1021/jo048035v
