(R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

Base Information

• Chemical Name: (R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester
• CAS No.: 537711-69-6
• Molecular Formula: C₁₈H₂₆O₄
• Molecular Weight: 306.402
• Mol file: 537711-69-6.mol

Synonyms:(R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

Chemical Property of (R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

There total 15 articles about (R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-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: 90.0%

methyl chloroformate (79-22-1) + (R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid (537711-65-2) → (R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester (537711-69-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1055/s-2003-37129

Reference yield:

1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hex-5-en-3-ol → (R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester (537711-69-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 79 percent / imidazole / CH₂Cl₂ / 20 °C

2.1: H₃B*SMe₂ / tetrahydrofuran / 20 °C

2.2: 81 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 20 °C

3.1: 92 percent / Bu₃P / CH₂Cl₂ / 20 °C

4.1: 83 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 20 °C

5.1: LDA / tetrahydrofuran / 0 °C

5.2: 82 percent / tetrahydrofuran / 0 °C

6.1: 88 percent / DMAP; Et₃N / 20 °C

7.1: 82 percent / Na/Hg; NaH₂PO₄ / methanol / -20 °C

8.1: 75 percent / PPTS / methanol / 0 °C

9.1: 96 percent / imidazole / CH₂Cl₂ / 20 °C

10.1: I₂; Ag₂CO₃ / toluene / 4 h / -20 °C

10.2: Bu₃SnH; Et₃B / tetrahydrofuran / 20 °C

11.1: 91 percent / KF; Jones reagent / acetone / 0 °C

12.1: 90 percent / DMAP; Et₃N / CH₂Cl₂ / 0 °C

With 1H-imidazole; dmap; potassium fluoride; sodium dihydrogenphosphate; sodium amalgam; jones reagent; tributylphosphine; dimethylsulfide borane complex; iodine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

DOI:10.1055/s-2003-37129

Reference yield:

(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-4-triethylsilanyloxy-hex-1-ene (537711-56-1) → (R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester (537711-69-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: H₃B*SMe₂ / tetrahydrofuran / 20 °C

1.2: 81 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 20 °C

2.1: 92 percent / Bu₃P / CH₂Cl₂ / 20 °C

3.1: 83 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 20 °C

4.1: LDA / tetrahydrofuran / 0 °C

4.2: 82 percent / tetrahydrofuran / 0 °C

5.1: 88 percent / DMAP; Et₃N / 20 °C

6.1: 82 percent / Na/Hg; NaH₂PO₄ / methanol / -20 °C

7.1: 75 percent / PPTS / methanol / 0 °C

8.1: 96 percent / imidazole / CH₂Cl₂ / 20 °C

9.1: I₂; Ag₂CO₃ / toluene / 4 h / -20 °C

9.2: Bu₃SnH; Et₃B / tetrahydrofuran / 20 °C

10.1: 91 percent / KF; Jones reagent / acetone / 0 °C

11.1: 90 percent / DMAP; Et₃N / CH₂Cl₂ / 0 °C

With 1H-imidazole; dmap; potassium fluoride; sodium dihydrogenphosphate; sodium amalgam; jones reagent; tributylphosphine; dimethylsulfide borane complex; iodine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

DOI:10.1055/s-2003-37129

upstream raw materials:

methyl chloroformate

(R)-2-[(2R,5S)-5-((S)-2-Benzyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid

(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-4-triethylsilanyloxy-hex-1-ene

(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-4-triethylsilanyloxy-hexan-1-ol