(+)-methyl (2E,5S)-5-(2-benzyloxyethyl)-4-oxaoct-2,7-dienoate

Base Information

• Chemical Name: (+)-methyl (2E,5S)-5-(2-benzyloxyethyl)-4-oxaoct-2,7-dienoate
• CAS No.: 1020267-38-2
• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.359
• Mol file: 1020267-38-2.mol

Synonyms:(+)-methyl (2E,5S)-5-(2-benzyloxyethyl)-4-oxaoct-2,7-dienoate

Chemical Property of (+)-methyl (2E,5S)-5-(2-benzyloxyethyl)-4-oxaoct-2,7-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-methyl (2E,5S)-5-(2-benzyloxyethyl)-4-oxaoct-2,7-dienoate

There total 1 articles about (+)-methyl (2E,5S)-5-(2-benzyloxyethyl)-4-oxaoct-2,7-dienoate 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: 87.0%

3-Benzyloxypropanal (19790-60-4) + propynoic acid methyl ester (922-67-8) + allylmagnesium bromide (1730-25-2) → (+)-methyl (2E,5S)-5-(2-benzyloxyethyl)-4-oxaoct-2,7-dienoate (1020267-38-2)

Guidance literature:

allylmagnesium bromide; With (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 2h; Inert atmosphere;

3-Benzyloxypropanal; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 2.75h; Inert atmosphere;

propynoic acid methyl ester; Further stages;

DOI:10.1021/ol800386d

Reference yield:

(+)-methyl (2E,5S)-5-(2-benzyloxyethyl)-4-oxaoct-2,7-dienoate (1020267-38-2) → methyl (2R,4R,6R)-[6-(2-benzyloxyethyl)-4-hydroxy-tetrahydropyran-2-yl]acetate (1020267-40-6) + methyl (2R,4S,6R)-[6-(2-benzyloxyethyl)-4-hydroxy-tetrahydropyran-2-yl]acetate (1020267-39-3)

Guidance literature:

(+)-methyl (2E,5S)-5-(2-benzyloxyethyl)-4-oxaoct-2,7-dienoate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

With potassium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.1021/ol800386d

upstream raw materials:

3-Benzyloxypropanal

propynoic acid methyl ester

allylmagnesium bromide

Downstream raw materials:

methyl (2R,4R,6R)-[6-(2-benzyloxyethyl)-4-hydroxy-tetrahydropyran-2-yl]acetate

methyl (2R,4S,6R)-[6-(2-benzyloxyethyl)-4-hydroxy-tetrahydropyran-2-yl]acetate