(4S,5S)-(E)-5-(2-ethenyl-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl)pent-2-en-1-ol

Base Information

Chemical Name:(4S,5S)-(E)-5-(2-ethenyl-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl)pent-2-en-1-ol
CAS No.:299178-71-5
Molecular Formula:C₂₄H₃₀N₂O
Molecular Weight:362.515
Hs Code.:

Synonyms:(4S,5S)-(E)-5-(2-ethenyl-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl)pent-2-en-1-ol

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Chemical Property of (4S,5S)-(E)-5-(2-ethenyl-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl)pent-2-en-1-ol

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Technology Process of (4S,5S)-(E)-5-(2-ethenyl-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl)pent-2-en-1-ol

There total 11 articles about (4S,5S)-(E)-5-(2-ethenyl-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl)pent-2-en-1-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:

Reference yield: 100.0%

: 299178-70-4
(4S,5S)-(E)-ethyl 5-(2-ethenyl-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl)pent-2-enoate

: 299178-71-5
(4S,5S)-(E)-5-(2-ethenyl-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl)pent-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 - 20 ℃;
DOI:10.1021/ol0001517

Reference yield:

: 52340-78-0
(R,R)-hydroxybenzoin

: 299178-71-5
(4S,5S)-(E)-5-(2-ethenyl-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl)pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: SOCl₂; Et₃N / CCl₄; H₂O; acetonitrile

1.2: 81 percent / RuCl₂*3(H₂O)2; NaIO₄ / CCl₄; H₂O; acetonitrile

2.1: 1.28 g / toluene / Heating

3.1: n-BuLi / tetrahydrofuran; hexane / 0.03 h / -78 °C

3.2: 99 percent / tetrahydrofuran; hexane / 0.5 h

4.1: n-BuLi / tetrahydrofuran; hexane / 0.03 h / -78 °C

4.2: 93 percent / tetrahydrofuran; hexane / 0.5 h

5.1: 100 percent / tetrahydrofuran / 2 h / 20 °C

6.1: tetrahydrofuran / 0.5 h / 20 °C

7.1: 0.4411 g / TBAF / tetrahydrofuran / 0.08 h

8.1: H₂ / Pd/BaSO₄ / ethyl acetate; pyridine / 0.5 h

8.2: 98 percent / TBAF / tetrahydrofuran

9.1: 100 percent / DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

10.1: 100 percent / CH₂Cl₂ / 20 °C

11.1: 100 percent / DIBAL / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; thionyl chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; Pd-BaSO₄; In tetrahydrofuran; pyridine; tetrachloromethane; hexane; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 1.1: Substitution / 1.2: Oxidation / 2.1: Substitution / 3.1: Metallation / 3.2: Methylation / 4.1: Metallation / 4.2: Alkylation / 5.1: Methylation / 6.1: Addition / 7.1: Substitution / 8.1: Catalytic hydrogenation / 8.2: Decomposition / 9.1: Swern oxidation / 10.1: Wittig olefination / 11.1: Reduction;
DOI:10.1021/ol0001517

Reference yield:

: 109830-48-0,133815-21-1
(4S,5S)-4,5-dihydro-2-methyl-4,5-diphenyl-1H-imidazole

: 299178-71-5
(4S,5S)-(E)-5-(2-ethenyl-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl)pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.03 h / -78 °C

1.2: 99 percent / tetrahydrofuran; hexane / 0.5 h

2.1: n-BuLi / tetrahydrofuran; hexane / 0.03 h / -78 °C

2.2: 93 percent / tetrahydrofuran; hexane / 0.5 h

3.1: 100 percent / tetrahydrofuran / 2 h / 20 °C

4.1: tetrahydrofuran / 0.5 h / 20 °C

5.1: 0.4411 g / TBAF / tetrahydrofuran / 0.08 h

6.1: H₂ / Pd/BaSO₄ / ethyl acetate; pyridine / 0.5 h

6.2: 98 percent / TBAF / tetrahydrofuran

7.1: 100 percent / DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

8.1: 100 percent / CH₂Cl₂ / 20 °C

9.1: 100 percent / DIBAL / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; Pd-BaSO₄; In tetrahydrofuran; pyridine; hexane; dichloromethane; ethyl acetate; 1.1: Metallation / 1.2: Methylation / 2.1: Metallation / 2.2: Alkylation / 3.1: Methylation / 4.1: Addition / 5.1: Substitution / 6.1: Catalytic hydrogenation / 6.2: Decomposition / 7.1: Swern oxidation / 8.1: Wittig olefination / 9.1: Reduction;
DOI:10.1021/ol0001517