(3Z,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-ol

Base Information

Chemical Name:(3Z,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-ol
CAS No.:809285-69-6
Molecular Formula:C₃₀H₄₈O₃Si
Molecular Weight:484.795
Hs Code.:

Synonyms:(3Z,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-ol

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Chemical Property of (3Z,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-ol

Chemical Property:

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Technology Process of (3Z,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-ol

There total 12 articles about (3Z,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-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:

: 1-[(Z)-(1S,3S)-2,2-Dimethyl-1-((E)-propenyl)-3-triethylsilanyloxy-8-triisopropylsilanyl-oct-5-en-7-ynyloxymethyl]-4-methoxy-benzene

: 809285-69-6
(3Z,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-ol

: (3E,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-ol

Guidance literature:: With chloroacetic acid; In methanol; dichloromethane; at 20 ℃; for 14h;
DOI:10.1021/ja0443068

Reference yield:

: 82192-59-4
1,3-bis(triisopropylsilyl)prop-1-yne

: 809285-69-6
(3Z,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-ol

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: 96.8 mg / chloroacetic acid / methanol; CH₂Cl₂ / 14 h / 20 °C

With n-butyllithium; chloroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Peterson olefination;
DOI:10.1021/ja0443068

Reference yield:

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

: 809285-69-6
(3Z,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-ol

Guidance literature:: Multi-step reaction with 8 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

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

7.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

8.1: 96.8 mg / chloroacetic acid / methanol; CH₂Cl₂ / 14 h / 20 °C

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; potassium hexamethylsilazane; acetic acid; dimethyl sulfoxide; triethylamine; chloroacetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 6.1: Swern oxidation / 7.1: Peterson olefination;
DOI:10.1021/ja0443068