2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanone

Base Information

• Chemical Name: 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanone
• CAS No.: 849676-36-4
• Molecular Formula: C₂₂H₄₂O₃Si
• Molecular Weight: 382.659

Synonyms:2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanone

Chemical Property of 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanone

There total 9 articles about 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanone 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: 96.0%

methyl iodide (74-88-4) + 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-hydroxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanone (849676-35-3) → 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanone (849676-36-4)

Guidance literature:

With silver(l) oxide; In diethyl ether; at 40 ℃; for 3h;

DOI:10.1021/jo047858h

Reference yield:

4-hydroxymethyl-cyclohexanone (38580-68-6) → 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanone (849676-36-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 75 percent / imidazole / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

2.1: (+)-bis(α-methylbenzylamine) hydrochloride; BuLi / tetrahydrofuran / 2 h / -100 - -95 °C

3.1: 1.37 g / O₂ / Pd(OAc)2 / dimethylsulfoxide / 16 h / 20 °C

4.1: t-BuLi; lithium 2-thienylcyanocuprate / pentane; tetrahydrofuran / 0.5 h / -78 °C

4.2: pentane; tetrahydrofuran / 0.5 h

5.1: KHCO₃; mCPBA / CH₂Cl₂ / 1 h / 0 °C

5.2: 1.04 g / TFA / methanol; tetrahydrofuran

6.1: 96 percent / Ag₂O / diethyl ether / 3 h / 40 °C

With 1H-imidazole; n-butyllithium; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; tert.-butyl lithium; oxygen; potassium hydrogencarbonate; thien-2-yl(cyano)copper lithium; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane;

DOI:10.1021/jo047858h

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanone (849676-36-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 75 percent / imidazole / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

2.1: (+)-bis(α-methylbenzylamine) hydrochloride; BuLi / tetrahydrofuran / 2 h / -100 - -95 °C

3.1: 1.37 g / O₂ / Pd(OAc)2 / dimethylsulfoxide / 16 h / 20 °C

4.1: t-BuLi; lithium 2-thienylcyanocuprate / pentane; tetrahydrofuran / 0.5 h / -78 °C

4.2: pentane; tetrahydrofuran / 0.5 h

5.1: KHCO₃; mCPBA / CH₂Cl₂ / 1 h / 0 °C

5.2: 1.04 g / TFA / methanol; tetrahydrofuran

6.1: 96 percent / Ag₂O / diethyl ether / 3 h / 40 °C

With 1H-imidazole; n-butyllithium; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; tert.-butyl lithium; oxygen; potassium hydrogencarbonate; thien-2-yl(cyano)copper lithium; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane;

DOI:10.1021/jo047858h

upstream raw materials:

methyl iodide

2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-hydroxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanone

isopentyl iodide

4-hydroxymethyl-cyclohexanone

Downstream raw materials:

1(S)-2(S)-3(S)-2-(1,5-dimethyl-hex-1-enyl)-3-methoxy-4-oxo-cyclohexanecarbaldehyde

2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-methoxy-4-(1-hydroxy-ethyl)-cyclohexanone

2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-methoxy-4-(2,2,2-trifluoro-acetyl)-cyclohexanone

1(R)-2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol

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