(S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyl ester

Base Information

• Chemical Name: (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyl ester
• CAS No.: 760181-75-7
• Molecular Formula: C₃₄H₅₂O₅Si
• Molecular Weight: 568.869
• Mol file: 760181-75-7.mol

Synonyms:(S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyl ester

Chemical Property of (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyl ester

There total 6 articles about (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyl 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: 89.0%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-hydroxy-pent-4-enyl ester (760181-80-4) → (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyl ester (760181-75-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 4.5h;

DOI:10.1016/j.tet.2004.05.045

Reference yield:

(2S)-2,4-dibenzyloxybutanal (109199-96-4) → (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyl ester (760181-75-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: KOH; AgNO₃ / methanol; H₂O / 0.33 h / 0 °C

2.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

2.2: 77 percent / DMAP / tetrahydrofuran; toluene / 3 h / 20 °C

3.1: 91 percent / NaHCO₃; DDQ / CH₂Cl₂ / 5 h / 0 °C

4.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 4.5 h / 20 °C

With 2,6-dimethylpyridine; potassium hydroxide; 2,4,6-trichlorobenzoyl chloride; sodium hydrogencarbonate; silver nitrate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.tet.2004.05.045

Reference yield:

(R)-2-(4-methoxybenzyloxy)pent-4-en-1-ol (760181-72-4) → (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyl ester (760181-75-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 1.3 g / ZnBr₂ / diethyl ether / 2 h / 0 °C

3.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

3.2: 77 percent / DMAP / tetrahydrofuran; toluene / 3 h / 20 °C

4.1: 91 percent / NaHCO₃; DDQ / CH₂Cl₂ / 5 h / 0 °C

5.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 4.5 h / 20 °C

With 2,6-dimethylpyridine; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc dibromide; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Swern oxidation / 2.1: Grignard reaction;

DOI:10.1016/j.tet.2004.05.045

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

(S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-hydroxy-pent-4-enyl ester

(2S)-2,4-dibenzyloxybutanal

(R)-2-(4-methoxybenzyloxy)pent-4-en-1-ol

Downstream raw materials:

Chloro-acetic acid (S)-2,4-bis-benzyloxy-1-((1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyloxy)-butyl ester