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

Base Information

• Chemical Name: 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-hydroxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanone
• CAS No.: 849676-35-3
• Molecular Formula: C₂₁H₄₀O₃Si
• Molecular Weight: 368.632
• Mol file: 849676-35-3.mol

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

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

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

3(R)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-triethylsilanyloxy-cyclohexene (849676-34-2) → 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-hydroxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanone (872603-35-5) + 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-hydroxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanone (849676-35-3)

Guidance literature:

3(R)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-triethylsilanyloxy-cyclohexene; With potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h;

With trifluoroacetic acid; In tetrahydrofuran; methanol; at 0 ℃; for 0.5h;

Reference yield:

3(R)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-triethylsilanyloxy-cyclohexene (849676-34-2) → 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-hydroxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanone (849676-35-3)

Guidance literature:

3(R)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-triethylsilanyloxy-cyclohexene; With potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h;

With trifluoroacetic acid; In tetrahydrofuran; methanol;

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)-2-hydroxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanone (849676-35-3)

Guidance literature:

Multi-step reaction with 5 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

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; palladium diacetate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane;

DOI:10.1021/jo047858h

upstream raw materials:

3(R)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-triethylsilanyloxy-cyclohexene

isopentyl iodide

4-hydroxymethyl-cyclohexanone

tert-butyldimethylsilyl chloride

Downstream raw materials:

(E)-3-(4-Methoxy-phenyl)-acrylic acid (1R,2S,3S,4S)-3-((E)-1,5-dimethyl-hex-1-enyl)-4-hydroxymethyl-2-methoxy-cyclohexyl ester

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

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

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