2-Hydroxy-6-(3-methyl-but-2-enyl)-benzoic acid (E)-(S)-4-iodo-1-(2-triisopropylsilanyloxy-ethyl)-but-3-enyl ester

Base Information

Chemical Name:2-Hydroxy-6-(3-methyl-but-2-enyl)-benzoic acid (E)-(S)-4-iodo-1-(2-triisopropylsilanyloxy-ethyl)-but-3-enyl ester
CAS No.:852327-32-3
Molecular Formula:C₂₇H₄₃IO₄Si
Molecular Weight:586.626
Hs Code.:

Synonyms:2-Hydroxy-6-(3-methyl-but-2-enyl)-benzoic acid (E)-(S)-4-iodo-1-(2-triisopropylsilanyloxy-ethyl)-but-3-enyl ester

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Chemical Property of 2-Hydroxy-6-(3-methyl-but-2-enyl)-benzoic acid (E)-(S)-4-iodo-1-(2-triisopropylsilanyloxy-ethyl)-but-3-enyl ester

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Technology Process of 2-Hydroxy-6-(3-methyl-but-2-enyl)-benzoic acid (E)-(S)-4-iodo-1-(2-triisopropylsilanyloxy-ethyl)-but-3-enyl ester

There total 11 articles about 2-Hydroxy-6-(3-methyl-but-2-enyl)-benzoic acid (E)-(S)-4-iodo-1-(2-triisopropylsilanyloxy-ethyl)-but-3-enyl ester 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: 91.0%

: 852327-33-4
6-iodo-1-triisopropylsilanyloxy-hex-5-en-3-ol

: 569340-87-0
2,2-dimethyl-5-(3-methyl-but-2-enyl)-benzo[1,3]dioxin-4-one

: 852327-32-3
2-Hydroxy-6-(3-methyl-but-2-enyl)-benzoic acid (E)-(S)-4-iodo-1-(2-triisopropylsilanyloxy-ethyl)-but-3-enyl ester

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1021/jo0477751

Reference yield:

: 852327-34-5
Triisopropyl-((R)-2-oxiranyl-ethoxy)-silane

: 852327-32-3
2-Hydroxy-6-(3-methyl-but-2-enyl)-benzoic acid (E)-(S)-4-iodo-1-(2-triisopropylsilanyloxy-ethyl)-but-3-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: 90 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

2.1: 2789 mg / camphorsulfonic acid / CH₂Cl₂ / 12 h / 20 °C

3.1: 99 percent / K₂CO₃ / methanol / 1 h / 20 °C

4.1: Cp₂ZrHCl / CH₂Cl₂ / 0.75 h / 20 °C

4.2: 88 percent / I₂ / CH₂Cl₂; tetrahydrofuran / 0.33 h / 20 °C

5.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 0.5 h / 20 °C

6.1: 91 percent / NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

With Schwartz's reagent; n-butyllithium; camphor-10-sulfonic acid; sodium hexamethyldisilazane; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1021/jo0477751

Reference yield:

: 852327-35-6
(S)-1-Triisopropylsilanyloxy-6-trimethylsilanyl-hex-5-yn-3-ol

: 852327-32-3
2-Hydroxy-6-(3-methyl-but-2-enyl)-benzoic acid (E)-(S)-4-iodo-1-(2-triisopropylsilanyloxy-ethyl)-but-3-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2789 mg / camphorsulfonic acid / CH₂Cl₂ / 12 h / 20 °C

2.1: 99 percent / K₂CO₃ / methanol / 1 h / 20 °C

3.1: Cp₂ZrHCl / CH₂Cl₂ / 0.75 h / 20 °C

3.2: 88 percent / I₂ / CH₂Cl₂; tetrahydrofuran / 0.33 h / 20 °C

4.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 0.5 h / 20 °C

5.1: 91 percent / NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

With Schwartz's reagent; camphor-10-sulfonic acid; sodium hexamethyldisilazane; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo0477751