(-)-(1Z,2S,3S,4S,5S)-1-ethylidene-5-hydroxy-3-((1S)-1-phenylethoxy)-2,4,5-trimethylheptyl benzoate

Base Information

• Chemical Name: (-)-(1Z,2S,3S,4S,5S)-1-ethylidene-5-hydroxy-3-((1S)-1-phenylethoxy)-2,4,5-trimethylheptyl benzoate
• CAS No.: 1258965-40-0
• Molecular Formula: C₂₇H₃₆O₄
• Molecular Weight: 424.58
• Mol file: 1258965-40-0.mol

Synonyms:(-)-(1Z,2S,3S,4S,5S)-1-ethylidene-5-hydroxy-3-((1S)-1-phenylethoxy)-2,4,5-trimethylheptyl benzoate

Chemical Property of (-)-(1Z,2S,3S,4S,5S)-1-ethylidene-5-hydroxy-3-((1S)-1-phenylethoxy)-2,4,5-trimethylheptyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1Z,2S,3S,4S,5S)-1-ethylidene-5-hydroxy-3-((1S)-1-phenylethoxy)-2,4,5-trimethylheptyl benzoate

There total 4 articles about (-)-(1Z,2S,3S,4S,5S)-1-ethylidene-5-hydroxy-3-((1S)-1-phenylethoxy)-2,4,5-trimethylheptyl benzoate 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: 90.0%

(-)-(1Z,2S,3R,4R)-1-ethylidene-2,4,6-trimethyl-5-oxo-3-((1S)-1-phenylethoxy)heptyl benzoate → (-)-(1Z,2S,3S,4S,5S)-1-ethylidene-5-hydroxy-3-((1S)-1-phenylethoxy)-2,4,5-trimethylheptyl benzoate (1258965-40-0)

Guidance literature:

With tri-n-butyl-tin hydride; dimethylaluminum chloride; In hexane; dichloromethane; at -78 - -60 ℃; for 50h; diastereoselective reaction;

DOI:10.1002/anie.201003735

Reference yield: 90.0%

C27H34O4 (1258965-55-7) → (-)-(1Z,2S,3S,4S,5S)-1-ethylidene-5-hydroxy-3-((1S)-1-phenylethoxy)-2,4,5-trimethylheptyl benzoate (1258965-40-0)

Guidance literature:

With tri-n-butyl-tin hydride; dimethylaluminum chloride; In dichloromethane; at -78 - -60 ℃; Inert atmosphere;

DOI:10.1021/jo102035d

Reference yield:

(E)-2-methyl-3-trimethylsilyloxypent-3-ene (19980-42-8) → (-)-(1Z,2S,3S,4S,5S)-1-ethylidene-5-hydroxy-3-((1S)-1-phenylethoxy)-2,4,5-trimethylheptyl benzoate (1258965-40-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sulfur dioxide; bis(trifluoromethanesulfonyl)amide; allyl-trimethyl-silane / dichloromethane; toluene / -78 °C / Inert atmosphere

1.2: Inert atmosphere; Reflux

2.1: tri-n-butyl-tin hydride; dimethylaluminum chloride / dichloromethane / -78 - -60 °C / Inert atmosphere

With sulfur dioxide; tri-n-butyl-tin hydride; dimethylaluminum chloride; bis(trifluoromethanesulfonyl)amide; allyl-trimethyl-silane; In dichloromethane; toluene;

DOI:10.1021/jo102035d

upstream raw materials:

C₂₇H₃₄O₄

(E)-2-methyl-3-trimethylsilyloxypent-3-ene

(-)-(1E,3Z,1'S)-2-methyl-1-(1'-phenylethoxy)penta-1,3-dien-3-yl benzoate

Downstream raw materials:

(-)-(2R,3S,4S,5R,6S)-2-ethyl-6-isopropyl-3,5-dimethyl-4-((1S)-1-phenylethoxy)tetrahydro-2H-pyran-2-ol

(-)-(1Z,2S,3S,4R,5S)-5-[(allyloxycarbonyl)oxy]-1-ethylidene-3-[(1S)-1-phenylethoxy]-2,4,6-trimethylheptyl benzoate

(+)-(2Z,4S,5S,6S,7S)-5,7-dihydroxy-4,6,8-trimethylnon-2-en-3-yl benzoate

(+)-(2Z,4S)-4-[(4S,5S,6S)-2,2,5-trimethyl-6-(propan-2-yl)-1,3-dioxan-4-yl]pent-2-en-3-yl benzoate