2-Hexenoic acid, 2-methyl-6-(phenylmethoxy)-, ethyl ester, (2E)-

Base Information

• Chemical Name: 2-Hexenoic acid, 2-methyl-6-(phenylmethoxy)-, ethyl ester, (2E)-
• CAS No.: 109307-90-6
• Molecular Formula: C16H22O3
• Molecular Weight: 262.349
• Mol file: 109307-90-6.mol

Synonyms:

Chemical Property of 2-Hexenoic acid, 2-methyl-6-(phenylmethoxy)-, ethyl ester, (2E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Hexenoic acid, 2-methyl-6-(phenylmethoxy)-, ethyl ester, (2E)-

There total 8 articles about 2-Hexenoic acid, 2-methyl-6-(phenylmethoxy)-, ethyl ester, (2E)- 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: 75.0%

4-benzyloxybutanal (5470-84-8) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → ethyl 2-methyl-6-(phenylmethoxy)-2(E)-hexenoate (109307-90-6)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2013.01.134

Reference yield:

4-benzyloxybutanal (5470-84-8) + 2-diethoxyphosphoryl-propionic acid ethyl ester; sodium enolate (67492-95-9) → ethyl 2-methyl-6-(phenylmethoxy)-2(E)-hexenoate (109307-90-6)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 2h; Yield given;

DOI:10.1021/jo00304a022

Reference yield:

ethyl 2-diethoxyphosphorylpropionate (3699-66-9) + 4-benzyloxybutanal (5470-84-8) → ethyl 2-methyl-6-(phenylmethoxy)-2(E)-hexenoate (109307-90-6)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) dimethoxyethane, 30 min, 2.) dimethoxyethane, 1 h;

DOI:10.1021/jo00228a040

upstream raw materials:

ethyl 2-diethoxyphosphorylpropionate

4-benzyloxy-butan-1-ol

4-benzyloxybutanal

2-diethoxyphosphoryl-propionic acid ethyl ester; sodium enolate

Downstream raw materials:

2-methyl-6-(phenylmethoxy)-2(E)-hexen-1-ol

ethyl (2S,3R)-6-benzyloxy-2,3-dihydroxy-2-methylhexanoate

ethyl (4S,5R)-5-[3-(benzyloxy)propyl]-2,2,4-trimethyl-1,3-dioxolane-4-carboxylate

(2R,3S)-6-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylhexanal

Refernces

• 1、 Yadav,Raju,Ravindar,Subba Reddy. "A formal stereoselective synthesis of (-)-brevisamide". supporting information. p. 3227 - 3229. Retrieved 2013/06/27.
• 2、 Mulzer,Karig,Pojarliev. "A novel highly stereoselective total synthesis of epothilone B and of its (12R, 13R) acetonide". . p. 7635 - 7638. Retrieved 2007/10/03.