Technology Process of (6Z,8Z,10E,14Z,17Z)-(5S,12R)-5,12-Dihydroxy-icosa-6,8,10,14,17-pentaenoic acid
There total 18 articles about (6Z,8Z,10E,14Z,17Z)-(5S,12R)-5,12-Dihydroxy-icosa-6,8,10,14,17-pentaenoic acid which
guide to synthetic route it.
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synthetic route:
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80445-66-5,88763-91-1,88763-92-2,92008-52-1,109958-18-1,109958-19-2,109958-20-5,126721-43-5,126721-44-6,144489-46-3,150447-94-2
(6Z,8Z,10E,14Z,17Z)-(5S,12R)-5,12-Dihydroxy-icosa-6,8,10,14,17-pentaenoic acid
- Guidance literature:
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Multi-step reaction with 5 steps
1: 90 percent / zinc amalgum, anhydrous hydrogen chloride / diethyl ether / 2 h / 0 °C
2: 1.) LiOH; 2.) H2 / 2.) 10percent Pd-C / 1.) DME, 25 deg C, 2 h; 2.) 1 atm, ethylacetate
3: 78 percent / pyridinium dichromate, anhydrous magnesium sulfate, 4A mol.siev. / CH2Cl2 / 1.5 h / 23 °C
5: 1.) potassium isopropoxide; 2.) base / 1.) 0 deg C, 1 h; 2.) hydrolysis
With
hydrogenchloride; lithium hydroxide; amalgamated zinc; dipyridinium dichromate; 4A mol.siev; hydrogen; potassium isopropoxide; magnesium sulfate;
palladium on activated charcoal;
In
diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(01)99801-6
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80445-66-5,88763-91-1,88763-92-2,92008-52-1,109958-18-1,109958-19-2,109958-20-5,126721-43-5,126721-44-6,144489-46-3,150447-94-2
(6Z,8Z,10E,14Z,17Z)-(5S,12R)-5,12-Dihydroxy-icosa-6,8,10,14,17-pentaenoic acid
- Guidance literature:
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Multi-step reaction with 11 steps
1: 90 percent / tetrahydrofuran / 12 h / 65 °C
2: 91 percent / LiAlH4 / diethyl ether / 5 h / 25 °C
3: 76 percent / dimethyl(S,S)(-)-tartarate
4: 90 percent / H2 / Lindlar / tetrahydrofuran / 760 Torr
5: 84 percent / O2 / oxidation with Collins reagent
6: 94 percent / tetrahydrofuran / -78 deg C, 10 min,; and then from -78 deg Cto 0 deg C over 1 h.
7: 84 percent / acetic acid; acetonitrile; H2O / 6 h / 25 °C
8: triphenylphosphine, imidazole, I2, diisopropylamine / diethyl ether; acetonitrile / 0.67 h / 25 °C
9: acetonitrile / 16 h / 60 °C
11: 1.) potassium isopropoxide; 2.) base / 1.) 0 deg C, 1 h; 2.) hydrolysis
With
1H-imidazole; lithium aluminium tetrahydride; Dimethyl D-tartrate; hydrogen; iodine; oxygen; potassium isopropoxide; diisopropylamine; triphenylphosphine;
Lindlar's catalyst;
In
tetrahydrofuran; diethyl ether; water; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(01)99801-6
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80445-66-5,88763-91-1,88763-92-2,92008-52-1,109958-18-1,109958-19-2,109958-20-5,126721-43-5,126721-44-6,144489-46-3,150447-94-2
(6Z,8Z,10E,14Z,17Z)-(5S,12R)-5,12-Dihydroxy-icosa-6,8,10,14,17-pentaenoic acid
- Guidance literature:
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Multi-step reaction with 13 steps
1: triphenyl phosphite, I2, imidazol / diethyl ether; acetonitrile / 0.67 h / 25 °C
2: Cu(I)
3: 90 percent / tetrahydrofuran / 12 h / 65 °C
4: 91 percent / LiAlH4 / diethyl ether / 5 h / 25 °C
5: 76 percent / dimethyl(S,S)(-)-tartarate
6: 90 percent / H2 / Lindlar / tetrahydrofuran / 760 Torr
7: 84 percent / O2 / oxidation with Collins reagent
8: 94 percent / tetrahydrofuran / -78 deg C, 10 min,; and then from -78 deg Cto 0 deg C over 1 h.
9: 84 percent / acetic acid; acetonitrile; H2O / 6 h / 25 °C
10: triphenylphosphine, imidazole, I2, diisopropylamine / diethyl ether; acetonitrile / 0.67 h / 25 °C
11: acetonitrile / 16 h / 60 °C
13: 1.) potassium isopropoxide; 2.) base / 1.) 0 deg C, 1 h; 2.) hydrolysis
With
1H-imidazole; triphenyl phosphite; lithium aluminium tetrahydride; Dimethyl D-tartrate; hydrogen; iodine; oxygen; potassium isopropoxide; diisopropylamine; triphenylphosphine;
Lindlar's catalyst; copper;
In
tetrahydrofuran; diethyl ether; water; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(01)99801-6
