2-[(Z)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-3-(tetrahydro-pyran-2-yloxy)-phenol

Base Information

Chemical Name:2-[(Z)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-3-(tetrahydro-pyran-2-yloxy)-phenol
CAS No.:289472-29-3
Molecular Formula:C₂₉H₃₈O₅
Molecular Weight:466.618
Hs Code.:

Synonyms:2-[(Z)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-3-(tetrahydro-pyran-2-yloxy)-phenol

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Chemical Property of 2-[(Z)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-3-(tetrahydro-pyran-2-yloxy)-phenol

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Technology Process of 2-[(Z)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-3-(tetrahydro-pyran-2-yloxy)-phenol

There total 14 articles about 2-[(Z)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-3-(tetrahydro-pyran-2-yloxy)-phenol 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: 65.0%

: 289472-28-2
C₃₀H₄₀O₅

: 289472-29-3
2-[(Z)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-3-(tetrahydro-pyran-2-yloxy)-phenol

Guidance literature:: With sodium thioethylate; In N,N-dimethyl-formamide; for 5.5h; Heating;
DOI:10.1016/S0040-4039(00)00676-6

Reference yield:

: 78916-50-4
1,3-dimethoxy-5-(2-phenylethyl)benzene

: 289472-29-3
2-[(Z)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-3-(tetrahydro-pyran-2-yloxy)-phenol

Guidance literature:: Multi-step reaction with 9 steps

1.1: sec-BuLi; TMEDA / tetrahydrofuran

1.2: 91 percent / tetrahydrofuran

2.1: 87 percent / MgI₂*Et₂O / benzene / 3 h / Heating

3.1: NaH / tetrahydrofuran / 2 h / 20 °C

4.1: NaBH₄ / ethanol / 2.5 h / 0 °C

5.1: PBr₃; pyridine / diethyl ether / 0.5 h / 0 °C

6.1: 68 percent / Pd₂(dba)3; AsPh₃ / 1,2-dimethoxy-ethane / 24 h / 85 °C

7.1: 97 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

8.1: 80 percent / PPTS / CH₂Cl₂ / 3 h / 0 °C

9.1: 65 percent / NaSEt / dimethylformamide / 5.5 h / Heating

With pyridine; sodium tetrahydroborate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; N,N,N,N,-tetramethylethylenediamine; triphenyl-arsane; tetrabutyl ammonium fluoride; sec.-butyllithium; pyridinium p-toluenesulfonate; phosphorus tribromide; sodium hydride; magnesium iodide; sodium thioethylate; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Metallation / 1.2: Formylation / 2.1: demethylation / 3.1: silylation / 4.1: Reduction / 5.1: Bromination / 6.1: Stille coupling / 7.1: desilylation / 8.1: alkenylation / 9.1: demethylation;
DOI:10.1016/S0040-4039(00)00676-6

Reference yield:

: 289472-07-7
2,6-dimethoxy-4-(2-phenylethyl)benzaldehyde

: 289472-29-3
2-[(Z)-3-Methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-5-phenethyl-3-(tetrahydro-pyran-2-yloxy)-phenol

Guidance literature:: Multi-step reaction with 8 steps

1: 87 percent / MgI₂*Et₂O / benzene / 3 h / Heating

2: NaH / tetrahydrofuran / 2 h / 20 °C

3: NaBH₄ / ethanol / 2.5 h / 0 °C

4: PBr₃; pyridine / diethyl ether / 0.5 h / 0 °C

5: 68 percent / Pd₂(dba)3; AsPh₃ / 1,2-dimethoxy-ethane / 24 h / 85 °C

6: 97 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

7: 80 percent / PPTS / CH₂Cl₂ / 3 h / 0 °C

8: 65 percent / NaSEt / dimethylformamide / 5.5 h / Heating

With pyridine; sodium tetrahydroborate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; triphenyl-arsane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; phosphorus tribromide; sodium hydride; magnesium iodide; sodium thioethylate; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: demethylation / 2: silylation / 3: Reduction / 4: Bromination / 5: Stille coupling / 6: desilylation / 7: alkenylation / 8: demethylation;
DOI:10.1016/S0040-4039(00)00676-6