Technology Process of (2S,3S)-(4E)-1,2-cyclohexylidenedioxy-3,5-bis(4-methoxyphenyl)pent-4-ene
There total 13 articles about (2S,3S)-(4E)-1,2-cyclohexylidenedioxy-3,5-bis(4-methoxyphenyl)pent-4-ene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
methanesulfonyl chloride;
In
pyridine;
at 20 ℃;
for 14h;
DOI:10.3987/COM-00-9015
- Guidance literature:
-
Multi-step reaction with 9 steps
1: CuCN / diethyl ether / 0.5 h / -20 °C
2: 70 percent / imidazole / CH2Cl2 / 24 h / 20 °C
3: 66 percent / tetrahydrofuran / 3.5 h / 20 °C
4: 70 percent / OsO4; NMO / acetonitrile; H2O / 43 h / 20 °C
5: 94 percent / NaIO4 / methanol; H2O / 2.5 h / 20 °C
6: 182 mg / LiAlH4 / tetrahydrofuran / 21.5 h / 20 °C
7: TBAF / tetrahydrofuran / 1.5 h / ice-cooling
8: 53 mg / CSA / dimethylformamide / 7.5 h / 50 °C
9: MsCl / pyridine / 3 h / Heating
With
1H-imidazole; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; methanesulfonyl chloride;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
1: Grignard reaction / 2: Etherification / 3: Grignard reaction / 4: Oxidation / 5: Oxidation / 6: Reduction / 7: Hydrolysis / 8: Etherification / 9: Dehydration;
DOI:10.3987/COM-00-8907
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 6 percent / DBU / benzene / 5 h / Heating
2: 70 percent / imidazole / CH2Cl2 / 24 h / 20 °C
3: 66 percent / tetrahydrofuran / 3.5 h / 20 °C
4: 70 percent / OsO4; NMO / acetonitrile; H2O / 43 h / 20 °C
5: 94 percent / NaIO4 / methanol; H2O / 2.5 h / 20 °C
6: 182 mg / LiAlH4 / tetrahydrofuran / 21.5 h / 20 °C
7: TBAF / tetrahydrofuran / 1.5 h / ice-cooling
8: 53 mg / CSA / dimethylformamide / 7.5 h / 50 °C
9: MsCl / pyridine / 3 h / Heating
With
1H-imidazole; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;
1: Ring cleavage / 2: Etherification / 3: Grignard reaction / 4: Oxidation / 5: Oxidation / 6: Reduction / 7: Hydrolysis / 8: Etherification / 9: Dehydration;
DOI:10.3987/COM-00-8907
