(2S,3R,4S,5R)-3-(tert-butyldimethylsilyloxy)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4-dimethylcyclohexanone

Base Information

Chemical Name:(2S,3R,4S,5R)-3-(tert-butyldimethylsilyloxy)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4-dimethylcyclohexanone
CAS No.:851450-10-7
Molecular Formula:C₃₃H₅₄O₅Si
Molecular Weight:558.874
Hs Code.:

(2S,3R,4S,5R)-3-(tert-butyldimethylsilyloxy)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4-dimethylcyclohexanone

Synonyms:(2S,3R,4S,5R)-3-(tert-butyldimethylsilyloxy)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4-dimethylcyclohexanone

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Chemical Property of (2S,3R,4S,5R)-3-(tert-butyldimethylsilyloxy)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4-dimethylcyclohexanone

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Technology Process of (2S,3R,4S,5R)-3-(tert-butyldimethylsilyloxy)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4-dimethylcyclohexanone

There total 5 articles about (2S,3R,4S,5R)-3-(tert-butyldimethylsilyloxy)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4-dimethylcyclohexanone 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:

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

: 851450-10-7
(2S,3R,4S,5R)-3-(tert-butyldimethylsilyloxy)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4-dimethylcyclohexanone

Guidance literature:: Multi-step reaction with 4 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

With bromine; tert.-butyl lithium; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol050236d

Reference yield:

: 851450-16-3
(Z)-2,5-dimethylhex-2-enoic acid

: 851450-10-7
(2S,3R,4S,5R)-3-(tert-butyldimethylsilyloxy)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4-dimethylcyclohexanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: Br₂ / CH₂Cl₂ / -78 °C

2.1: 73 percent / NaHCO₃ / dimethylformamide / 65 °C

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

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

3.3: 60 percent / tetrahydrofuran; pentane; diethyl ether / 180 h / -50 - 0 °C

With bromine; tert.-butyl lithium; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol050236d

Reference yield:

: threo-2,3-dibromo-2,5-dimethylhexanoic acid

: 851450-10-7
(2S,3R,4S,5R)-3-(tert-butyldimethylsilyloxy)-5-[(E)-1,4-dimethylpent-1-enyl]-6-[(2S)-3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4-dimethylcyclohexanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: 73 percent / NaHCO₃ / dimethylformamide / 65 °C

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

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

2.3: 60 percent / tetrahydrofuran; pentane; diethyl ether / 180 h / -50 - 0 °C

With tert.-butyl lithium; sodium hydrogencarbonate; In tetrahydrofuran; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol050236d