Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate

Base Information

• Chemical Name: Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate
• CAS No.: 152187-07-0
• Molecular Formula: C₁₉H₃₄O₃Si
• Molecular Weight: 338.563
• Mol file: 152187-07-0.mol

Synonyms:Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate

Chemical Property of Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate

There total 4 articles about Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate 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:

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene (152187-06-9) → Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate (152187-07-0)

Guidance literature:

With triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 75 ℃; for 22h;

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) → Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate (152187-07-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 1) iPr₂NLi / 1) THF, hexane, 1 h, -78 deg C, 2) THF, 5 h, 0 deg C

3: Et₃N / PdCl₂(Ph₃P)2 / dimethylformamide / 22 h / 75 °C

With dmap; triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one (130583-95-8) → Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate (152187-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) iPr₂NLi / 1) THF, hexane, 1 h, -78 deg C, 2) THF, 5 h, 0 deg C

2: Et₃N / PdCl₂(Ph₃P)2 / dimethylformamide / 22 h / 75 °C

With triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide;

upstream raw materials:

acrylic acid methyl ester

(R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene

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

(4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one

Downstream raw materials:

(E)-<3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)allyl>sulfonylbenzene

(E)-3-[(R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]allyl acetate

(2Z,4E)-5-(4-Hydroxy-2,6,6-trimethylcyclohex-1-enyl)-3-methoxycarbonylpenta-2,4-dienal

(E)-3-((R)-4-Acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-acrylic acid methyl ester