Propanoic acid, 2-methyl-, (1Z)-1-[(1E)-1-methyl-2-[(1S)-1-phenylethoxy]ethenyl]-1-propenyl ester

Base Information

• Chemical Name: Propanoic acid, 2-methyl-, (1Z)-1-[(1E)-1-methyl-2-[(1S)-1-phenylethoxy]ethenyl]-1-propenyl ester
• CAS No.: 767319-35-7
• Molecular Formula: C18H24O3
• Molecular Weight: 288.387
• Mol file: 767319-35-7.mol

Synonyms:

Chemical Property of Propanoic acid, 2-methyl-, (1Z)-1-[(1E)-1-methyl-2-[(1S)-1-phenylethoxy]ethenyl]-1-propenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Propanoic acid, 2-methyl-, (1Z)-1-[(1E)-1-methyl-2-[(1S)-1-phenylethoxy]ethenyl]-1-propenyl ester

There total 3 articles about Propanoic acid, 2-methyl-, (1Z)-1-[(1E)-1-methyl-2-[(1S)-1-phenylethoxy]ethenyl]-1-propenyl ester 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: 97.0%

isobutyryl chloride (79-30-1) + (S)-(1E)-2-methyl-1-(1-(phenyl)ethoxy)pent-1-en-3-one → (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol isobutyrate (767319-35-7)

Guidance literature:

(S)-(1E)-2-methyl-1-(1-(phenyl)ethoxy)pent-1-en-3-one; With N,N,N,N,-tetramethylethylenediamine; sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.5h;

isobutyryl chloride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo901878b

Reference yield: 87.0%

isobutyryl fluoride (430-92-2) + C17H26O2Si → (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol isobutyrate (767319-35-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -15 ℃; for 0.5h;

DOI:10.1021/jo901878b

Reference yield:

(S)-(1E)-2-methyl-1-(1-(phenyl)ethoxy)pent-1-en-3-one → (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol isobutyrate (767319-35-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; diethyl ether;

DOI:10.1002/chem.200400825

upstream raw materials:

isobutyryl fluoride

isobutyryl chloride

Downstream raw materials:

Isobutyric acid (Z)-(2S,3R,4S)-1-eth-(Z)-ylidene-2,4-dimethyl-3-((S)-1-phenyl-ethoxy)-5-trimethylsilanyloxy-hept-5-enyl ester

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

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

Refernces

• 1、 Turks, Maris,Huang, Xiaogen,Vogel, Pierre. "Expeditious asymmetric synthesis of a stereoheptad corresponding to the C(19)-C(27)-ansa chain of rifamycins: Formal total synthesis of rifamycin S". . p. 465 - 476. Retrieved 2007/10/03.