(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol

Base Information

• Chemical Name: (1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol
• CAS No.: 205172-20-9
• Molecular Formula: C₂₂H₄₆O₃Si₂
• Molecular Weight: 414.776
• Mol file: 205172-20-9.mol

Synonyms:(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol

Chemical Property of (1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol

There total 3 articles about (1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol 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:

(6R)-levodione (60046-49-3) → (1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol (205172-20-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / H₂ / Raney-Ni (W₂-activity) / methanol / 1 h

2: 81.2 percent / aq. HCl (37percent) / CH₂Cl₂ / 1.17 h / Ambient temperature

3: 85.5 percent / imidazole / dimethylformamide / 1.5 h

4: 1.) tri-n-butylstannane, azobis(isobutyronitrile, 2.) n-BuLi / 1) 130 deg C, 16 h; 2) THF, hexane, -78 deg C, 90 min; 3) THF, hexane, -78 deg C, 2 h

With 1H-imidazole; hydrogenchloride; n-butyllithium; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; Raney-Ni (W₂-activity); In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/np970517x

Reference yield:

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one (20548-02-1,55058-51-0,60686-81-9,60686-82-0,82977-53-5,90082-06-7,90129-05-8,99881-84-2,60046-50-6) → (1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol (205172-20-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 81.2 percent / aq. HCl (37percent) / CH₂Cl₂ / 1.17 h / Ambient temperature

2: 85.5 percent / imidazole / dimethylformamide / 1.5 h

3: 1.) tri-n-butylstannane, azobis(isobutyronitrile, 2.) n-BuLi / 1) 130 deg C, 16 h; 2) THF, hexane, -78 deg C, 90 min; 3) THF, hexane, -78 deg C, 2 h

With 1H-imidazole; hydrogenchloride; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/np970517x

Reference yield:

3-(trimethylsiloxy)but-1-yne (17869-76-0,100244-12-0,117924-32-0) + (+)-(4R,6S)-4-tert-butyldimethylsiloxy-2,2,6-trimethylcyclohexanone (130694-69-8) → (1R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((E)-3-hydroxy-but-1-enyl)-2,2,6-trimethyl-cyclohexanol + (1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((E)-3-hydroxy-but-1-enyl)-2,2,6-trimethyl-cyclohexanol + (1R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol (205172-19-6) + (1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol (205172-20-9)

Guidance literature:

With n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; Yield given. Multistep reaction. Yields of byproduct given; 1) 130 deg C, 16 h; 2) THF, hexane, -78 deg C, 90 min; 3) THF, hexane, -78 deg C, 2 h;

DOI:10.1021/np970517x

upstream raw materials:

3-(trimethylsiloxy)but-1-yne

(+)-(4R,6S)-4-tert-butyldimethylsiloxy-2,2,6-trimethylcyclohexanone

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

(6R)-levodione

Downstream raw materials:

(E)-4-[(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-but-3-en-2-one