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

Base Information

• Chemical Name: (+)-(4R,6S)-4-tert-butyldimethylsiloxy-2,2,6-trimethylcyclohexanone
• CAS No.: 130694-69-8
• Molecular Formula: C₁₅H₃₀O₂Si
• Molecular Weight: 270.488
• Mol file: 130694-69-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (+)-(4R,6S)-4-tert-butyldimethylsiloxy-2,2,6-trimethylcyclohexanone 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: 99.0%

1H-imidazole (288-32-4) + (+)-4(Z)-(4R,5S)-4-hydroxy-4-(5-hydroxy-3-methylpent-3-en-1-ynyl)-3,3,5-trimethylcyclohexanone (130694-71-2) + tert-butyldimethylsilyl chloride (18162-48-6) → (+)-(4R,6S)-4-tert-butyldimethylsiloxy-2,2,6-trimethylcyclohexanone (130694-69-8)

Guidance literature:

In N,N-dimethyl-formamide;

Reference yield: 99.0%

(+)-(4R,6S)-4-hydroxy-2,2,6-trimethylcyclohexanone (60686-81-9) + tert-butyldimethylsilyl chloride (18162-48-6) → (+)-(4R,6S)-4-tert-butyldimethylsiloxy-2,2,6-trimethylcyclohexanone (130694-69-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

Reference yield:

(6R)-levodione (60046-49-3) → (+)-(4R,6S)-4-tert-butyldimethylsiloxy-2,2,6-trimethylcyclohexanone (130694-69-8)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; hydrogenchloride; hydrogen; Raney-Ni (W₂-activity); In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/np970517x

upstream raw materials:

(+)-(4R,6S)-4-hydroxy-2,2,6-trimethylcyclohexanone

tert-butyldimethylsilyl chloride

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

(6R)-levodione

Downstream raw materials:

Acetic acid (Z)-5-[(1R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-pent-2-en-4-ynyl ester

(+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol

Acetic acid (Z)-5-((1R,6S)-1-hydroxy-2,2,6-trimethyl-4-oxo-cyclohexyl)-3-methyl-pent-2-en-4-ynyl ester

(+)-(4S,5S)-methyl dihydroabscisate