Benzoic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-pent-4-enyl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-pent-4-enyl ester
• CAS No.: 207591-96-6
• Molecular Formula: C₂₇H₂₆O₅
• Molecular Weight: 430.5
• Mol file: 207591-96-6.mol

Synonyms:Benzoic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-pent-4-enyl ester

Chemical Property of Benzoic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-pent-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-pent-4-enyl ester

There total 6 articles about Benzoic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-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: 91.0%

benzoyl chloride (98-88-4) + (2S,3R)-2-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-pent-4-ene-1,3-diol (207591-92-2) → Benzoic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-pent-4-enyl ester (207591-96-6)

Guidance literature:

With triethylamine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1271/bbb.62.521

Reference yield:

(2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one (195141-43-6) → Benzoic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-pent-4-enyl ester (207591-96-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / tetrahydrofuran; diethyl ether / 0.5 h / 5 °C

2: 88 percent / n-Bu₄NF / tetrahydrofuran / 0.5 h / 0 °C

3: 74 percent / PPh₃, I₂, imidazole / toluene / 1 h / Heating

4: 95 percent / Zn / ethanol / 0.5 h / Heating

5: 91 percent / Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; triethylamine; triphenylphosphine; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; toluene;

DOI:10.1271/bbb.62.521

Reference yield:

(2R,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-iodomethyl-tetrahydro-furan-3-ol (207591-91-1) → Benzoic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-pent-4-enyl ester (207591-96-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Zn / ethanol / 0.5 h / Heating

2: 91 percent / Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

With triethylamine; zinc; In ethanol; dichloromethane;

DOI:10.1271/bbb.62.521

upstream raw materials:

benzoyl chloride

(2S,3R)-2-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-pent-4-ene-1,3-diol

(2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one

(2R,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-iodomethyl-tetrahydro-furan-3-ol