Technology Process of 8-benzyloxy-8-(5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-butyl-4-methyl-octa-1,4,6-trien-3-ol
There total 15 articles about 8-benzyloxy-8-(5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-butyl-4-methyl-octa-1,4,6-trien-3-ol which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 87 percent / NaH / dimethylformamide / 2 h / 0 °C
2: 79 percent / Grubbs' second-generation catalyst / CH2Cl2 / 18 h / Heating
3: 72 percent / H2 / Pd/C / ethyl acetate / 2 h
4: 85 percent / DDQ / CH2Cl2; H2O / 4 h / 20 °C
5: 2-iodoxybenzoic acid / dimethylsulfoxide; tetrahydrofuran / 5 h
6: LDA / tetrahydrofuran / 2 h / -78 °C
7: 91 percent / DIBAL-H / CH2Cl2 / 1 h / -78 °C
8: 2-iodoxybenzoic acid / dimethylsulfoxide; tetrahydrofuran / 2 h / 20 °C
9: CrCl2; NiCl / dimethylsulfoxide / 24 h / 20 °C
With
chromium dichloride; hydrogen; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel(I) chloride; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
6: Wittig-Horner reaction / 9: Nozaki-Hiyama-Kishi coupling reaction;
DOI:10.1055/s-2007-967968
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 72 percent / H2 / Pd/C / ethyl acetate / 2 h
2: 85 percent / DDQ / CH2Cl2; H2O / 4 h / 20 °C
3: 2-iodoxybenzoic acid / dimethylsulfoxide; tetrahydrofuran / 5 h
4: LDA / tetrahydrofuran / 2 h / -78 °C
5: 91 percent / DIBAL-H / CH2Cl2 / 1 h / -78 °C
6: 2-iodoxybenzoic acid / dimethylsulfoxide; tetrahydrofuran / 2 h / 20 °C
7: CrCl2; NiCl / dimethylsulfoxide / 24 h / 20 °C
With
chromium dichloride; hydrogen; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel(I) chloride; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;
4: Wittig-Horner reaction / 7: Nozaki-Hiyama-Kishi coupling reaction;
DOI:10.1055/s-2007-967968
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 79 percent / Grubbs' second-generation catalyst / CH2Cl2 / 18 h / Heating
2: 72 percent / H2 / Pd/C / ethyl acetate / 2 h
3: 85 percent / DDQ / CH2Cl2; H2O / 4 h / 20 °C
4: 2-iodoxybenzoic acid / dimethylsulfoxide; tetrahydrofuran / 5 h
5: LDA / tetrahydrofuran / 2 h / -78 °C
6: 91 percent / DIBAL-H / CH2Cl2 / 1 h / -78 °C
7: 2-iodoxybenzoic acid / dimethylsulfoxide; tetrahydrofuran / 2 h / 20 °C
8: CrCl2; NiCl / dimethylsulfoxide / 24 h / 20 °C
With
chromium dichloride; hydrogen; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel(I) chloride; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;
5: Wittig-Horner reaction / 8: Nozaki-Hiyama-Kishi coupling reaction;
DOI:10.1055/s-2007-967968
