benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate

Base Information

• Chemical Name: benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate
• CAS No.: 1339946-92-7
• Molecular Formula: C₃₀H₂₈O₅
• Molecular Weight: 468.549
• Mol file: 1339946-92-7.mol

Synonyms:benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate

Chemical Property of benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate

There total 9 articles about benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate 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: 60.0%

benzyl (2R,3S)-2,3-dihydroxy-3-(3,4-dibenzyloxyphenyl)-propionate (1241892-06-7) → benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate (1339946-92-7)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 6.5h;

DOI:10.1016/j.molstruc.2017.09.118

Reference yield:

(R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropionic acid benzyl ester (1339947-25-9) + benzyl bromide (100-39-0) → benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate (1339946-92-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃;

Reference yield:

benzyl bromide (100-39-0) → benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate (1339946-92-7)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / ethanol / 24 h / Reflux

2: pyridine; piperidine / toluene / 6 h / Reflux

3: sodium sulfite; methanesulfonamide / acetone; acetonitrile; water / 24 h / 20 °C

4: triethylsilane; trifluoroacetic acid / dichloromethane / 6.5 h / 0 - 20 °C

With piperidine; pyridine; triethylsilane; methanesulfonamide; potassium carbonate; trifluoroacetic acid; sodium sulfite; In ethanol; dichloromethane; water; acetone; toluene; acetonitrile;

DOI:10.1016/j.molstruc.2017.09.118

upstream raw materials:

(E)-benzyl 3-(3,4-bis(benzyloxy)phenyl)acrylate

benzyl alcohol

benzyl bromide

3,4-dihydroxybenzaldehyde

Downstream raw materials:

C₃₄H₃₄O₆

C₃₄H₃₄O₆

C₃₁H₃₂N₂O₅

C₁₂H₁₄O₆

Refernces

• 1、 Sidoryk, Katarzyna,Filip, Katarzyna,Cmoch, Piotr,?aszcz, Marta,Cybulski, Marcin. "Efficient synthesis and physicochemical characterization of natural danshensu, its S isomer and intermediates thereof". . p. 135 - 148. Retrieved 2017/10/13.