(E)-(3S,5S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-oct-6-enal

Base Information

Chemical Name:(E)-(3S,5S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-oct-6-enal
CAS No.:809285-83-4
Molecular Formula:C₂₄H₄₀O₄Si
Molecular Weight:420.665
Hs Code.:

Synonyms:(E)-(3S,5S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-oct-6-enal

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Chemical Property of (E)-(3S,5S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-oct-6-enal

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Technology Process of (E)-(3S,5S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-oct-6-enal

There total 10 articles about (E)-(3S,5S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-oct-6-enal 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:

: 1-[(1S,3S)-2,2-Dimethyl-1-((E)-propenyl)-3,5-bis-triethylsilanyloxy-pentyloxymethyl]-4-methoxy-benzene

: 809285-83-4
(E)-(3S,5S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-oct-6-enal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 0.916667h;
DOI:10.1021/ja0443068

Reference yield:

: 220367-70-4
(4S)-4-(2-methyl-1-hydroxyprop-2-yl)-2,2-dimethyl[1,3]dioxane

: 809285-83-4
(E)-(3S,5S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-oct-6-enal

Guidance literature:: Multi-step reaction with 7 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2.5 h / -78 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

2.2: 2.315 g / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

3.1: 83 percent / Red-Al / tetrahydrofuran; toluene / 25 h / Heating

4.1: Et₃N; KHMDS / tetrahydrofuran / 3 h / -78 - 20 °C

5.1: 2.20 g / aq. AcOH / tetrahydrofuran / 12 h / 60 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 152.0 mg / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.92 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; potassium hexamethylsilazane; acetic acid; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: Swern oxidation / 7.1: Swern oxidation;
DOI:10.1021/ja0443068

Reference yield:

: 185148-92-9
(S)-2-(2,2-dimethyl-<1,3>dioxan-4-yl)-2-methylpropionaldehyde

: 809285-83-4
(E)-(3S,5S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-oct-6-enal

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

1.2: 2.315 g / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

2.1: 83 percent / Red-Al / tetrahydrofuran; toluene / 25 h / Heating

3.1: Et₃N; KHMDS / tetrahydrofuran / 3 h / -78 - 20 °C

4.1: 2.20 g / aq. AcOH / tetrahydrofuran / 12 h / 60 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 152.0 mg / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.92 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; potassium hexamethylsilazane; acetic acid; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; toluene; 6.1: Swern oxidation;
DOI:10.1021/ja0443068