(E)-(3S,4R)-2-Methyl-6-phenyl-4-triethylsilanyloxy-hex-5-en-3-ol

Base Information

• Chemical Name: (E)-(3S,4R)-2-Methyl-6-phenyl-4-triethylsilanyloxy-hex-5-en-3-ol
• CAS No.: 181714-75-0
• Molecular Formula: C₁₉H₃₂O₂Si
• Molecular Weight: 320.547
• Mol file: 181714-75-0.mol

Synonyms:(E)-(3S,4R)-2-Methyl-6-phenyl-4-triethylsilanyloxy-hex-5-en-3-ol

Chemical Property of (E)-(3S,4R)-2-Methyl-6-phenyl-4-triethylsilanyloxy-hex-5-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(3S,4R)-2-Methyl-6-phenyl-4-triethylsilanyloxy-hex-5-en-3-ol

There total 3 articles about (E)-(3S,4R)-2-Methyl-6-phenyl-4-triethylsilanyloxy-hex-5-en-3-ol 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:

(+/-)-(1E,4E)-1-Phenylhexa-1,4-diene-3-ol → (E)-(3S,4R)-2-Methyl-6-phenyl-4-triethylsilanyloxy-hex-5-en-3-ol (181714-75-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 43 percent / molecular sieves 3 Angstroem, CaH₂, Ti(O-iPr)4, D-(-)-DIPT, TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 °C

2: 96 percent / imidazole / CH₂Cl₂ / 0.17 h / Ambient temperature

3: 1.) CuI / 1.) Et₂O, 0 deg C, 10 min, 2.) 0 deg C, 30 min

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; calcium hydride; 3 A molecular sieve; D-(-)-diisopropyl tartrate; In 2,2,4-trimethylpentane; dichloromethane;

DOI:10.1039/p19960001729

Reference yield:

(1E,3R,4R,5R)-1,2-Epoxy-1-phenylhex-4-en-3-ol (173657-96-0) → (E)-(3S,4R)-2-Methyl-6-phenyl-4-triethylsilanyloxy-hex-5-en-3-ol (181714-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / imidazole / CH₂Cl₂ / 0.17 h / Ambient temperature

2: 1.) CuI / 1.) Et₂O, 0 deg C, 10 min, 2.) 0 deg C, 30 min

With 1H-imidazole; copper(l) iodide; In dichloromethane;

DOI:10.1039/p19960001729

Reference yield:

methyllithium (917-54-4) + Triethyl-[(E)-(R)-1-((2S,3R)-3-methyl-oxiranyl)-3-phenyl-allyloxy]-silane (181714-74-9) → (E)-(3S,4R)-2-Methyl-6-phenyl-4-triethylsilanyloxy-hex-5-en-3-ol (181714-75-0) + (E)-(2S,3R,4S)-3-Methyl-6-phenyl-4-triethylsilanyloxy-hex-5-en-2-ol

Guidance literature:

With copper(l) iodide; Yield given. Multistep reaction; 1.) Et₂O, 0 deg C, 10 min, 2.) 0 deg C, 30 min;

DOI:10.1039/p19960001729

upstream raw materials:

methyllithium

Triethyl-[(E)-(R)-1-((2S,3R)-3-methyl-oxiranyl)-3-phenyl-allyloxy]-silane

(1E,3R,4R,5R)-1,2-Epoxy-1-phenylhex-4-en-3-ol

Downstream raw materials:

(3R,4S)-3,4-Isopropylidenedioxy-5-methyl-1-phenylhex-1-ene

(E)-(3R,4S)-5-Methyl-1-phenyl-hex-1-ene-3,4-diol