(1S,2S)-1-((S)-6-allyl-6-methylcyclohex-1-enyl)-2-hydroxy-5-methyl-2-(2-methylpent-3-yn-2-yl)hex-4-enyl benzoate

Base Information

Chemical Name:(1S,2S)-1-((S)-6-allyl-6-methylcyclohex-1-enyl)-2-hydroxy-5-methyl-2-(2-methylpent-3-yn-2-yl)hex-4-enyl benzoate
CAS No.:1612869-08-5
Molecular Formula:C₃₀H₄₀O₃
Molecular Weight:448.646
Hs Code.:

Synonyms:(1S,2S)-1-((S)-6-allyl-6-methylcyclohex-1-enyl)-2-hydroxy-5-methyl-2-(2-methylpent-3-yn-2-yl)hex-4-enyl benzoate

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Chemical Property of (1S,2S)-1-((S)-6-allyl-6-methylcyclohex-1-enyl)-2-hydroxy-5-methyl-2-(2-methylpent-3-yn-2-yl)hex-4-enyl benzoate

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Technology Process of (1S,2S)-1-((S)-6-allyl-6-methylcyclohex-1-enyl)-2-hydroxy-5-methyl-2-(2-methylpent-3-yn-2-yl)hex-4-enyl benzoate

There total 11 articles about (1S,2S)-1-((S)-6-allyl-6-methylcyclohex-1-enyl)-2-hydroxy-5-methyl-2-(2-methylpent-3-yn-2-yl)hex-4-enyl benzoate 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: 93.0%

: 1612868-99-1
(4S,5S)-5-((S)-6-allyl-6-methylcyclohex-1-enyl)-4-(3-methylbut-2-enyl)-4-(2-methylpent-3-yn-2-yl)-1,3-dioxolan-2-one

: 591-51-5
phenyllithium

: 1612869-08-5
(1S,2S)-1-((S)-6-allyl-6-methylcyclohex-1-enyl)-2-hydroxy-5-methyl-2-(2-methylpent-3-yn-2-yl)hex-4-enyl benzoate

Guidance literature:: In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h;
DOI:10.1021/ol501304j

Reference yield:

: 1612868-73-1
2,6,6-trimethylnon-2-en-7-yn-5-one

: 1612869-08-5
(1S,2S)-1-((S)-6-allyl-6-methylcyclohex-1-enyl)-2-hydroxy-5-methyl-2-(2-methylpent-3-yn-2-yl)hex-4-enyl benzoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: zinc(II) iodide / dichloromethane / 2 h / Reflux

2.1: diisobutylaluminium hydride / hexane / 0.5 h / -78 - 0 °C

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / -78 - 20 °C

3.2: 5 h / -78 °C

3.3: 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C

5.1: Amberlyst H-15 / methanol / 48 h / 20 °C

6.1: tributylphosphine / tetrahydrofuran / 0.33 h / 20 °C

7.1: ammonium molybdate; dihydrogen peroxide / tetrahydrofuran; water / 0.33 h / -10 °C

8.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

With ammonium molybdate; tributylphosphine; dihydrogen peroxide; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; zinc(II) iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; pentane; 3.1: |Shapiro Olefination / 3.3: |Shapiro Olefination;
DOI:10.1021/ol501304j

Reference yield:

: 1612868-75-3
5-methyl-2-(2-methylpent-3-yn-2-yl)-2-(trimethylsilyloxy)hex-4-enal

: 1612869-08-5
(1S,2S)-1-((S)-6-allyl-6-methylcyclohex-1-enyl)-2-hydroxy-5-methyl-2-(2-methylpent-3-yn-2-yl)hex-4-enyl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / -78 - 20 °C

1.2: 5 h / -78 °C

1.3: 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C

3.1: Amberlyst H-15 / methanol / 48 h / 20 °C

4.1: tributylphosphine / tetrahydrofuran / 0.33 h / 20 °C

5.1: ammonium molybdate; dihydrogen peroxide / tetrahydrofuran; water / 0.33 h / -10 °C

6.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

With ammonium molybdate; tributylphosphine; dihydrogen peroxide; tert.-butyl lithium; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; mineral oil; pentane; 1.1: |Shapiro Olefination / 1.3: |Shapiro Olefination;
DOI:10.1021/ol501304j