(4S,5R,6S)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-hydroxy-2-methylpropionyl]-2,4,6-trimethylcyclohex-2-enone

Base Information

Chemical Name:(4S,5R,6S)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-hydroxy-2-methylpropionyl]-2,4,6-trimethylcyclohex-2-enone
CAS No.:851450-20-9
Molecular Formula:C₂₀H₃₂O₃
Molecular Weight:320.472
Hs Code.:

Synonyms:(4S,5R,6S)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-hydroxy-2-methylpropionyl]-2,4,6-trimethylcyclohex-2-enone

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Chemical Property of (4S,5R,6S)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-hydroxy-2-methylpropionyl]-2,4,6-trimethylcyclohex-2-enone

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Technology Process of (4S,5R,6S)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-hydroxy-2-methylpropionyl]-2,4,6-trimethylcyclohex-2-enone

There total 7 articles about (4S,5R,6S)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-hydroxy-2-methylpropionyl]-2,4,6-trimethylcyclohex-2-enone 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%

: 851450-08-3
(4S,5R,6S)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4,6-trimethylcyclohex-2-enone

: 851450-20-9
(4S,5R,6S)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-hydroxy-2-methylpropionyl]-2,4,6-trimethylcyclohex-2-enone

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; pH=7;
DOI:10.1021/ol050236d

Reference yield:

: 851450-14-1
(Z)-2-bromo-5-methylhex-2-ene

: 851450-20-9
(4S,5R,6S)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-hydroxy-2-methylpropionyl]-2,4,6-trimethylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 6 steps

1.1: t-BuLi / diethyl ether / -78 °C

1.2: 94 percent / diethyl ether

2.1: Br₂ / CH₂Cl₂ / -78 °C

3.1: 73 percent / NaHCO₃ / dimethylformamide / 65 °C

4.1: t-BuLi / tetrahydrofuran; pentane / 0.25 h / -100 °C

4.2: CuCN / tetrahydrofuran; pentane; diethyl ether / 15 h / -50 °C

4.3: 60 percent / tetrahydrofuran; pentane; diethyl ether / 180 h / -50 - 0 °C

5.1: naH / tetrahydrofuran / 0.17 h / 20 °C

5.2: 77 percent / tetrahydrofuran / 16 h / 20 °C

6.1: 93 percent / DDQ / CH₂Cl₂ / pH 7

With bromine; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol050236d

Reference yield:

: 55642-36-9
(E)-2-bromo-5-methylhex-2-ene

: 851450-20-9
(4S,5R,6S)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-hydroxy-2-methylpropionyl]-2,4,6-trimethylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 3 steps

1.1: t-BuLi / tetrahydrofuran; pentane / 0.25 h / -100 °C

1.2: CuCN / tetrahydrofuran; pentane; diethyl ether / 15 h / -50 °C

1.3: 60 percent / tetrahydrofuran; pentane; diethyl ether / 180 h / -50 - 0 °C

2.1: naH / tetrahydrofuran / 0.17 h / 20 °C

2.2: 77 percent / tetrahydrofuran / 16 h / 20 °C

3.1: 93 percent / DDQ / CH₂Cl₂ / pH 7

With tert.-butyl lithium; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1021/ol050236d