(-)-(1Z,2S,3R,4R)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate

Base Information

• Chemical Name: (-)-(1Z,2S,3R,4R)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate
• CAS No.: 767319-40-4
• Molecular Formula: C₂₃H₃₄O₄
• Molecular Weight: 374.521
• Mol file: 767319-40-4.mol

Synonyms:(-)-(1Z,2S,3R,4R)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate

Chemical Property of (-)-(1Z,2S,3R,4R)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1Z,2S,3R,4R)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate

There total 4 articles about (-)-(1Z,2S,3R,4R)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate 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: 67.0%

(Z)-3-trimethylsiloxy-2-pentene (51425-54-8) + (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol isobutyrate (767319-35-7) → (-)-(1Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate (767319-38-0) + (-)-(1Z,2S,3R,4R)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate (767319-40-4)

Guidance literature:

(Z)-3-trimethylsiloxy-2-pentene; (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol isobutyrate; With sulfur dioxide; bis(trifluoromethanesulfonyl)amide; In dichloromethane; toluene; at -80 ℃; for 36h;

With potassium carbonate; triphenylphosphine; palladium diacetate; In dichloromethane; various solvents; toluene; for 0.333333h; Heating;

DOI:10.1021/ol048988f

Reference yield:

Trimethyl-{(Z)-1-[(E)-1-methyl-2-((S)-1-phenyl-ethoxy)-vinyl]-propenyloxy}-silane (681144-32-1) → (-)-(1Z,2S,3R,4R)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate (767319-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1: TBAF / tetrahydrofuran / 0.5 h / -15 °C

2: SO₂; (CF₃SO₂)2NH / toluene / 36 h / -80 °C

3: 0.9 g / K₂CO₃; Ph₃P / Pd(OAc)2 / toluene; acetonitrile; propan-2-ol / 0.33 h / Heating

With sulfur dioxide; tetrabutyl ammonium fluoride; potassium carbonate; bis(trifluoromethanesulfonyl)amide; triphenylphosphine; palladium diacetate; In tetrahydrofuran; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1002/chem.200400825

Reference yield:

(S)-(1E)-2-methyl-1-(1-(phenyl)ethoxy)pent-1-en-3-one → (-)-(1Z,2S,3R,4R)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate (767319-40-4)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / diethyl ether / 4 h / -20 - 0 °C

2: TBAF / tetrahydrofuran / 0.5 h / -15 °C

3: SO₂; (CF₃SO₂)2NH / toluene / 36 h / -80 °C

4: 0.9 g / K₂CO₃; Ph₃P / Pd(OAc)2 / toluene; acetonitrile; propan-2-ol / 0.33 h / Heating

With sulfur dioxide; tetrabutyl ammonium fluoride; potassium carbonate; bis(trifluoromethanesulfonyl)amide; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; diethyl ether; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1002/chem.200400825

upstream raw materials:

(Z)-3-trimethylsiloxy-2-pentene

(-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol isobutyrate

Trimethyl-{(Z)-1-[(E)-1-methyl-2-((S)-1-phenyl-ethoxy)-vinyl]-propenyloxy}-silane

Downstream raw materials:

(-)-(1R,2R,3R,4R,5R,6R)-1-ethyl-2,4,6-trimethyl-5-((1S)-1-phenylethoxy)cyclohexan-1,3-diol

(2S,3S,4R,5S,6S)-3-Ethyl-3-hydroxy-2,4,6-trimethyl-5-((S)-1-phenyl-ethoxy)-cyclohexanone