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

Base Information

• Chemical Name: (E)-3-[(R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]allyl acetate
• CAS No.: 152187-10-5
• Molecular Formula: C₂₀H₃₆O₃Si
• Molecular Weight: 352.59
• Mol file: 152187-10-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (E)-3-[(R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]allyl acetate 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:

acetic anhydride (108-24-7) + (-)-3-<(R)-4-(t-Butyl)dimethylsilyloxy-2,6,6-trimethyl-1-cyclohexen-1-yl>propen-1-ol (83021-09-4) → (E)-3-[(R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]allyl acetate (152187-10-5)

Guidance literature:

With pyridine; for 16h; Ambient temperature;

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) → (E)-3-[(R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]allyl acetate (152187-10-5)

Guidance literature:

Multi-step reaction with 5 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

4: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

5: pyridine / 16 h / Ambient temperature

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

Reference yield:

(4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one (130583-95-8) → (E)-3-[(R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]allyl acetate (152187-10-5)

Guidance literature:

Multi-step reaction with 4 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

3: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4: pyridine / 16 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In diethyl ether; N,N-dimethyl-formamide;

upstream raw materials:

acetic anhydride

(-)-3-<(R)-4-(t-Butyl)dimethylsilyloxy-2,6,6-trimethyl-1-cyclohexen-1-yl>propen-1-ol

(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:

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

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