Technology Process of (5S,14R,15S)-(6E,8Z,10E,12E)-5-O-tert-butyldiphenylsilyl-14,15-O-carbonyl lipoxin B4 ethyl ether
There total 17 articles about (5S,14R,15S)-(6E,8Z,10E,12E)-5-O-tert-butyldiphenylsilyl-14,15-O-carbonyl lipoxin B4 ethyl ether which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 2.) H2 / 2.) 5percent Pd-C / 1.) methylene dichloride
2: trifluoroacetic acid, water / tetrahydrofuran
3: lead tetraacetate / CH2Cl2 / -78 °C
4: toluene / 5 h / 80 °C
5: NaBH4-CeCl3 / propan-2-ol; H2O / 0 °C
6: DIPHOS, carbon tetrabromid / CH2Cl2 / Ambient temperature
7: acetonitrile
8: 1.) LiHMDS, 2.) HMPA / 1.) THF, -100 deg C, 2.) -40 deg C, 2 h
With
lead(IV) acetate; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; cerium(III) chloride; carbon tetrabromide; temephos; water; hydrogen; trifluoroacetic acid; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)99055-5
- Guidance literature:
-
Multi-step reaction with 9 steps
1: N-chlorosuccinimide/silver nitrate / acetonitrile; H2O / -20 °C
2: 2.) H2 / 2.) 5percent Pd-C / 1.) methylene dichloride
3: trifluoroacetic acid, water / tetrahydrofuran
4: lead tetraacetate / CH2Cl2 / -78 °C
5: toluene / 5 h / 80 °C
6: NaBH4-CeCl3 / propan-2-ol; H2O / 0 °C
7: DIPHOS, carbon tetrabromid / CH2Cl2 / Ambient temperature
8: acetonitrile
9: 1.) LiHMDS, 2.) HMPA / 1.) THF, -100 deg C, 2.) -40 deg C, 2 h
With
lead(IV) acetate; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; N-chloro-succinimide; cerium(III) chloride; carbon tetrabromide; temephos; water; hydrogen; silver nitrate; trifluoroacetic acid; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)99055-5
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 75 percent / BF3*OEt2 / diethyl ether / 1 h / -100 °C
2: 95 percent / H2 / PtO2 / ethanol
3: imidazole / dimethylformamide / 18 h / 80 °C
4: aq.TFA / tetrahydrofuran / 4 h / Ambient temperature
5: 95 percent / Pb(OAc)4 / CH2Cl2 / 1 h / 0 °C
6: 50 percent / toluene / 5 h / 80 °C
7: 97 percent / NaBH4, CeCl3 / propan-2-ol / 0 deg C to r.t.
8: CBr4, DIPHOS / CH2Cl2 / 1 h / -30 °C
9: acetonitrile / Ambient temperature
10: 1) KHMDS / 1) THF, -105 deg C, 2) HMPA, -100 to -40 deg C
With
1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; cerium(III) chloride; carbon tetrabromide; temephos; boron trifluoride diethyl etherate; hydrogen; potassium hexamethylsilazane; trifluoroacetic acid;
platinum(IV) oxide;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)92034-3
