Technology Process of (1E,3S,5Z)-2-methyl-6-trimethylsilyl-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol
There total 1 articles about (1E,3S,5Z)-2-methyl-6-trimethylsilyl-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 12 steps
1: 70 percent / DIBAL-H / CH2Cl2 / -78 °C
2: 90 percent / benzene / Heating
3: Bu3P(O); Et2AlCl; (S)-3,3'-(Ph2PO)2-1,1'-binaphthalene-2,2'-diol / CH2Cl2; hexane / 39 h / -40 °C
4: TFA / CH2Cl2; hexane / 1 h / 20 °C
5: 75 percent / H2SO4 / Heating
6: 99 percent / imidazole / dimethylformamide
7: 87 percent / DIBAL-H / toluene / -78 °C
8: tetrahydrofuran / -78 °C
9: tetrahydrofuran
10: 51 percent / HCO2NH4; Bu3P / Pd(OAc)2 / benzene / 50 °C
11: 89 percent / AcOH; H2O / tetrahydrofuran / 50 °C
12: 90 percent / [Ti(O-i-Pr)4]; i-PrMgCl / diethyl ether / -78 - -50 °C
With
1H-imidazole; titanium(IV) isopropylate; tributylphosphine; Tributylphosphine oxide; sulfuric acid; water; isopropylmagnesium chloride; ammonium formate; diethylaluminium chloride; diisobutylaluminium hydride; acetic acid; trifluoroacetic acid; 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-bis-diphenylphosphine oxide;
palladium diacetate;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
1: Reduction / 2: Condensation / 3: Addition / 4: Acidolysis / 5: Addition / 6: Etherification / 7: Reduction / 8: Addition / 9: Esterification / 10: Reductive deoxygenation / 11: Hydrolysis / 12: Reduction;
DOI:10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F
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312730-84-0
(3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate
- Guidance literature:
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Multi-step reaction with 3 steps
1.1: 59 percent / I2 / CH2Cl2 / 12 h / 20 °C
2.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C
3.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation
3.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C
With
dmap; 9-borabicyclo[3.3.1]nonane dimer; iodine; triethylamine;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/ja002024b
- Guidance literature:
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Multi-step reaction with 7 steps
1.1: 59 percent / I2 / CH2Cl2 / 12 h / 20 °C
2.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C
3.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation
3.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C
4.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C
5.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C
5.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h
6.1: 99 percent / HF*pyridine / tetrahydrofuran
7.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C
With
dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 2,4,6-trichlorobenzoyl chloride; iodine; 3,3-dimethyldioxirane; pyridine hydrogenfluoride; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja002024b
