(4S,5S)-3-(2-oxo-5-phenyl-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester

Base Information

• Chemical Name: (4S,5S)-3-(2-oxo-5-phenyl-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester
• CAS No.: 337508-79-9
• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.262
• Mol file: 337508-79-9.mol

Synonyms:(4S,5S)-3-(2-oxo-5-phenyl-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester

Chemical Property of (4S,5S)-3-(2-oxo-5-phenyl-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-3-(2-oxo-5-phenyl-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester

There total 2 articles about (4S,5S)-3-(2-oxo-5-phenyl-[1,3]dioxolan-4-yl)-acrylic acid ethyl 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%

bis(trichloromethyl) carbonate (32315-10-9) + ethyl (4S,5S)-4,5-dihydroxy-5-phenyl-2-pentenoate (337508-76-6) → (4S,5S)-3-(2-oxo-5-phenyl-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester (337508-79-9)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/ol0156188

Reference yield:

ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate (39806-16-1) → (4S,5S)-3-(2-oxo-5-phenyl-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester (337508-79-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / OsO₄; (DHQ)2PHAL; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 0 °C

2: 91 percent / pyridine; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

With pyridine; dmap; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In dichloromethane; water; tert-butyl alcohol; 1: Sharpless dihydroxylation;

DOI:10.1021/ol0156188

Reference yield: 72.0%

(4S,5S)-3-(2-oxo-5-phenyl-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester (337508-79-9) → (2E,5R)-5-hydroxy-5-phenyl-2-pentenoic acid ethyl ester (337508-81-3)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; formic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; for 2h; Heating;

DOI:10.1021/ol0156188

upstream raw materials:

bis(trichloromethyl) carbonate

ethyl (4S,5S)-4,5-dihydroxy-5-phenyl-2-pentenoate

ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate

Downstream raw materials:

(2E,5R)-5-hydroxy-5-phenyl-2-pentenoic acid ethyl ester