(S)-2-[(1-Benzyloxymethyl-cyclopropyl)-hydroxy-methyl]-3-isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester

Base Information

Chemical Name:(S)-2-[(1-Benzyloxymethyl-cyclopropyl)-hydroxy-methyl]-3-isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester
CAS No.:288401-41-2
Molecular Formula:C₂₇H₄₀O₄
Molecular Weight:428.612
Hs Code.:

Synonyms:(S)-2-[(1-Benzyloxymethyl-cyclopropyl)-hydroxy-methyl]-3-isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester

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Chemical Property of (S)-2-[(1-Benzyloxymethyl-cyclopropyl)-hydroxy-methyl]-3-isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester

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Technology Process of (S)-2-[(1-Benzyloxymethyl-cyclopropyl)-hydroxy-methyl]-3-isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester

There total 7 articles about (S)-2-[(1-Benzyloxymethyl-cyclopropyl)-hydroxy-methyl]-3-isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl 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: 81.0%

: 288401-35-4
(R)-3-Isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester

: 288401-39-8
1-[(phenylmethoxy)methyl]cyclopropanecarboxaldehyde

: 288401-41-2
(S)-2-[(1-Benzyloxymethyl-cyclopropyl)-hydroxy-methyl]-3-isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester

Guidance literature:: (R)-3-Isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2h;

1-[(phenylmethoxy)methyl]cyclopropanecarboxaldehyde; In tetrahydrofuran; at -78 ℃; for 0.166667h; Further stages.;
DOI:10.1021/ol006085q

Reference yield:

: 91201-40-0
Methyl (R)-3-(1-methylethyl)-6-oxoheptanoate

: 288401-41-2
(S)-2-[(1-Benzyloxymethyl-cyclopropyl)-hydroxy-methyl]-3-isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

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

2.1: Et₃N / DMAP / CH₂Cl₂ / 12 h / 20 °C

3.1: CuI / diethyl ether / 1 h / -30 °C

3.2: 236 mg / diethyl ether / 0.33 h / 20 °C

4.1: LDA / tetrahydrofuran / 2 h / -78 °C

4.2: 81 percent / tetrahydrofuran / 0.17 h / -78 °C

With copper(l) iodide; n-butyllithium; triethylamine; lithium diisopropyl amide; dmap; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Metallation / 1.2: Addition / 2.1: Acetylation / 3.1: Methylation / 3.2: Methylation / 4.1: Metallation / 4.2: Addition;
DOI:10.1021/ol006085q

Reference yield:

: (R)-6-Hydroxy-3-isopropyl-6-methyl-non-7-ynoic acid methyl ester

: 288401-41-2
(S)-2-[(1-Benzyloxymethyl-cyclopropyl)-hydroxy-methyl]-3-isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N / DMAP / CH₂Cl₂ / 12 h / 20 °C

2.1: CuI / diethyl ether / 1 h / -30 °C

2.2: 236 mg / diethyl ether / 0.33 h / 20 °C

3.1: LDA / tetrahydrofuran / 2 h / -78 °C

3.2: 81 percent / tetrahydrofuran / 0.17 h / -78 °C

With copper(l) iodide; triethylamine; lithium diisopropyl amide; dmap; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Acetylation / 2.1: Methylation / 2.2: Methylation / 3.1: Metallation / 3.2: Addition;
DOI:10.1021/ol006085q