Technology Process of (6E,8Z,11Z)-(S)-20-Amino-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester
There total 28 articles about (6E,8Z,11Z)-(S)-20-Amino-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 11 steps
1: 89 percent / PTSA / 2 h / 0 - 20 °C
2: 94 percent / acetonitrile / 38 h / 70 °C
3: 78 percent / LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C
4: 94 percent / TBAF / 28 h / 20 °C
5: 92 percent / PPh3; I2; imidazole / CH2Cl2 / 2 h / 0 - 20 °C
6: 95 percent / acetonitrile / 48 h / 70 °C
7: 85 percent / LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C
8: 75 percent / Me2AlCl / CH2Cl2 / 1.5 h / -30 - 20 °C
9: 88 percent / PPh3; I2; imidazole / CH2Cl2 / 0 - 20 °C
10: 89 percent / NaN3 / acetone / 16 h / 65 °C
11: 88 percent / PPh3 / H2O; tetrahydrofuran / 14 h / 20 °C
With
1H-imidazole; sodium azide; tetrabutyl ammonium fluoride; iodine; dimethylaluminum chloride; toluene-4-sulfonic acid; triphenylphosphine; lithium hexamethyldisilazane;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetone; acetonitrile;
1: acetalisation / 2: Substitution / 3: Wittig olefination / 4: Hydrolysis / 5: Substitution / 6: Substitution / 7: Wittig olefination / 8: acetal cleavage / 9: Substitution / 10: Substitution / 11: Reduction;
DOI:10.1016/S0040-4039(00)01064-9
- Guidance literature:
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Multi-step reaction with 13 steps
1: 97 percent / imidazole / CH2Cl2 / 0 - 20 °C
2: 100 percent / H5IO6 / diethyl ether; tetrahydrofuran / 0.25 h / 0 °C
3: 85 percent / benzene / 4 h / Heating
4: 100 percent / H2 / Pd/C
5: 92 percent / H5IO6 / diethyl ether; tetrahydrofuran / 18 h / 20 °C
6: 78 percent / benzene / Heating
7: 90 percent / LHDMS / -78 - 20 °C
8: 48 percent / 1N HCl / tetrahydrofuran; H2O / 40 h / 20 °C
9: 82 percent / pyridine / 0 - 20 °C
10: 99 percent / NaI / acetone / 99 h / 65 °C
11: 99 percent / acetonitrile / 65 °C
12: 36 percent / LHMDS / -78 - 20 °C
13: 88 percent / Ph3P / acetonitrile / 65 °C
With
pyridine; 1H-imidazole; hydrogenchloride; hydrogen; periodic acid; triphenylphosphine; sodium iodide; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; acetonitrile; benzene;
1: silylation / 2: Oxidation / 3: Condensation / 4: Catalytic hydrogenation / 5: Oxidation / 6: Condensation / 7: Condensation / 8: ether cleavage / 9: Esterification / 10: Substitution / 11: Addition / 12: Condensation / 13: Reduction;
DOI:10.1016/S0040-4039(00)00971-0
