(E)-4-[(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-yl]-4-oxo-but-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-4-[(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-yl]-4-oxo-but-2-enoic acid methyl ester
• CAS No.: 119243-96-8
• Molecular Formula: C₂₁H₂₈O₅
• Molecular Weight: 360.45
• Mol file: 119243-96-8.mol

Synonyms:(E)-4-[(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-yl]-4-oxo-but-2-enoic acid methyl ester

Chemical Property of (E)-4-[(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-yl]-4-oxo-but-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-[(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-yl]-4-oxo-but-2-enoic acid methyl ester

There total 6 articles about (E)-4-[(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-yl]-4-oxo-but-2-enoic acid methyl 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:

(4-Benzyloxy)butylmagnesium bromide → (E)-4-[(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-yl]-4-oxo-but-2-enoic acid methyl ester (119243-96-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) DMS*CuBr, TMEDA / 1.) Et₂O, -78 deg C, 2.) -78 deg C

2: 98 percent / DIBAL / CH₂Cl₂ / -78 °C

3: Ti(O-iPr)4, D-DIPT, t-BuOOH, 4-Angstroem sieves / CH₂Cl₂ / -50 °C

4: 1.) ClCOCOCl, DMSO, Et₃N, acid (traces)

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; acid (traces); diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1021/ja00187a081

Reference yield:

(R)-5-(2-Methoxy-ethoxymethoxy)-4-methyl-pent-1-yne (119243-76-4) → (E)-4-[(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-yl]-4-oxo-but-2-enoic acid methyl ester (119243-96-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1.) THF, -78 -> 78 deg C, 2.) -78 deg C

2: 1.) DMS*CuBr, TMEDA / 1.) Et₂O, -78 deg C, 2.) -78 deg C

3: 98 percent / DIBAL / CH₂Cl₂ / -78 °C

4: Ti(O-iPr)4, D-DIPT, t-BuOOH, 4-Angstroem sieves / CH₂Cl₂ / -50 °C

5: 1.) ClCOCOCl, DMSO, Et₃N, acid (traces)

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; acid (traces); diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1021/ja00187a081

Reference yield:

(R)-6-(2-Methoxy-ethoxymethoxy)-5-methyl-hex-2-ynoic acid methyl ester (119243-77-5) → (E)-4-[(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-yl]-4-oxo-but-2-enoic acid methyl ester (119243-96-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) DMS*CuBr, TMEDA / 1.) Et₂O, -78 deg C, 2.) -78 deg C

2: 98 percent / DIBAL / CH₂Cl₂ / -78 °C

3: Ti(O-iPr)4, D-DIPT, t-BuOOH, 4-Angstroem sieves / CH₂Cl₂ / -50 °C

4: 1.) ClCOCOCl, DMSO, Et₃N, acid (traces)

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; acid (traces); diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1021/ja00187a081

upstream raw materials:

{(2R,3S)-3-(4-Benzyloxy-butyl)-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-oxiranyl}-methanol

methyl (triphenylphosphoranylidene)acetate

(R)-5-(2-Methoxy-ethoxymethoxy)-4-methyl-pent-1-yne

(R)-6-(2-Methoxy-ethoxymethoxy)-5-methyl-hex-2-ynoic acid methyl ester