Technology Process of 3S,5,7S,9S-tetramethyl-11-benzyloxy-1-paramethoxybenzyloxy-2R,10R-bis-(tert-butyldimethylsiloxy)-4E-undecene
There total 16 articles about 3S,5,7S,9S-tetramethyl-11-benzyloxy-1-paramethoxybenzyloxy-2R,10R-bis-(tert-butyldimethylsiloxy)-4E-undecene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
5R-tert-butyldimethylsiloxy-2S,4S-dimethyl-6-benzyloxy-1-iodohexane;
With
tert.-butyl lithium; zinc(II) chloride;
In
diethyl ether; Petroleum ether;
at 20 ℃;
for 1h;
1-para-methoxybenzyloxy-2R-tert-butyldimethylsiloxy-3S-methyl-5E-iodohexene;
With
tetrakis(triphenylphosphine) palladium(0);
In
diethyl ether;
for 16h;
Further stages.;
DOI:10.1021/ja028941u
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 96 percent / triphenylphosphine; iodine; imidazole / acetonitrile; diethyl ether / 20 °C
2.1: LiCl; diisopropylamine; n-butyllithium / tetrahydrofuran; petroleum ether / 1.33 h / -78 - 20 °C
2.2: 93 percent / tetrahydrofuran; various solvent(s) / 40 h / 0 °C
3.1: 93 percent / diisopropylamine; n-butyllithium; borane-ammonium complex / tetrahydrofuran; petroleum ether / 2.17 h / 0 - 20 °C
4.1: 95 percent / triphenylphosphine; imidazole; iodine / diethyl ether; acetonitrile / 0.17 h / 20 °C
5.1: tert-butyllithium; ZnCl2 / diethyl ether; petroleum ether / 1 h / 20 °C
5.2: 58 percent / Pd(PPh3)4 / diethyl ether; various solvent(s) / 16 h
With
1H-imidazole; n-butyllithium; iodine; tert.-butyl lithium; diisopropylamine; triphenylphosphine; lithium chloride; zinc(II) chloride;
In
tetrahydrofuran; diethyl ether; acetonitrile; Petroleum ether;
2.1: Myer's alkylation / 5.2: Negishi coupling;
DOI:10.1021/ja028941u
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 94 percent / DIBAL-H / CH2Cl2 / 1.25 h / -78 - 0 °C
2.1: 96 percent / triphenylphosphine; iodine; imidazole / acetonitrile; diethyl ether / 20 °C
3.1: LiCl; diisopropylamine; n-butyllithium / tetrahydrofuran; petroleum ether / 1.33 h / -78 - 20 °C
3.2: 93 percent / tetrahydrofuran; various solvent(s) / 40 h / 0 °C
4.1: 93 percent / diisopropylamine; n-butyllithium; borane-ammonium complex / tetrahydrofuran; petroleum ether / 2.17 h / 0 - 20 °C
5.1: 95 percent / triphenylphosphine; imidazole; iodine / diethyl ether; acetonitrile / 0.17 h / 20 °C
6.1: tert-butyllithium; ZnCl2 / diethyl ether; petroleum ether / 1 h / 20 °C
6.2: 58 percent / Pd(PPh3)4 / diethyl ether; various solvent(s) / 16 h
With
1H-imidazole; n-butyllithium; iodine; tert.-butyl lithium; diisobutylaluminium hydride; diisopropylamine; triphenylphosphine; lithium chloride; zinc(II) chloride;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; Petroleum ether;
3.1: Myer's alkylation / 6.2: Negishi coupling;
DOI:10.1021/ja028941u
