2-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-propionic acid methyl ester

Base Information

• Chemical Name: 2-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-propionic acid methyl ester
• CAS No.: 919608-19-8
• Molecular Formula: C₂₄H₃₆O₅
• Molecular Weight: 404.547
• Mol file: 919608-19-8.mol

Synonyms:2-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-propionic acid methyl ester

Chemical Property of 2-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-propionic acid methyl ester

There total 21 articles about 2-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-propionic 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: 91.0%

3-[3-benzyloxy-1-(2-iodo-ethyl)-4-(5-methyl-tetrahydro-furan-2-yl)-pentyloxy]-2-methyl-acrylic acid methyl ester (919608-18-7) → 2-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-propionic acid methyl ester (919608-19-8)

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at -78 ℃; for 1h;

DOI:10.1002/anie.200602860

Reference yield: 91.0%

3-[3-benzyloxy-1-(2-iodo-ethyl)-4-(5-methyl-tetrahydro-furan-2-yl)-pentyloxy]-2-methyl-acrylic acid methyl ester (919608-18-7) → 2-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-propionic acid methyl ester (919608-19-8) + C24H36O5

Guidance literature:

With air; triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at -78 ℃;

DOI:10.1016/j.tet.2007.07.005

Reference yield:

methanesulfonic acid 5-(1-methyl-2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl ester (919608-15-4) → 2-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-propionic acid methyl ester (919608-19-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

1.2: 95 percent / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 66 percent / lithium aluminum hydride / diethyl ether / 0 - 20 °C

3.1: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0 - 20 °C

4.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

4.2: 97 percent / triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

5.1: 97 percent / magnesium bromide etherate / CH₂Cl₂ / 1 h / 20 °C

6.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

6.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

7.1: 851 mg / sodium borohydride / methanol / 0 - 20 °C

8.1: 92 percent / TEA / CH₂Cl₂ / 14 h / 0 °C

9.1: 89 percent / PPTS / benzene / 2 h / Heating

10.1: 90 percent / NaI / acetone / 2 h / Heating

11.1: 91 percent / n-Bu₃SnH; Et₃B; air / toluene; hexane / -78 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; air; triethyl borane; TEA; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; titanium tetrachloride; ozone; magnesium bromide ethyl etherate; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1016/j.tet.2007.07.005

upstream raw materials:

3-[3-benzyloxy-1-(2-iodo-ethyl)-4-(5-methyl-tetrahydro-furan-2-yl)-pentyloxy]-2-methyl-acrylic acid methyl ester

methanesulfonic acid 5-(1-methyl-2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl ester

2-(5-methyl-tetrahydro-furan-2-yl)-hex-5-en-3-ol

5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-pentane-1,3-diol

Downstream raw materials:

C₂₃H₃₅IO₃

2-[5-(3-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-2-oxo-butyl)-tetrahydro-furan-2-yl]-propionaldehyde

3-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-1-[5-(2-hydroxy-1-methyl-ethyl)-tetrahydro-furan-2-yl]-butan-2-ol

2-[5-(3-{5-[2-benzyloxy-3-(5-methyl-tetrahydro-furan-2-yl)-butyl]-tetrahydro-furan-2-yl}-2-oxo-butyl)-tetrahydro-furan-2-yl]-propionic acid