3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid

Base Information

• Chemical Name: 3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid
• CAS No.: 116511-71-8
• Molecular Formula: C₂₁H₃₈O₄Si₂
• Molecular Weight: 410.701
• Mol file: 116511-71-8.mol

Synonyms:3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid

Chemical Property of 3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid

There total 4 articles about 3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid 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: 99.0%

(E)-3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid (203118-32-5) → 3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid (116511-71-8)

Guidance literature:

With palladium on activated carbon; hydrogen; In ethyl acetate; for 3h;

DOI:10.3390/molecules20035038

Reference yield: 95.0%

dihydrocaffeic acid (1078-61-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid (116511-71-8)

Guidance literature:

dihydrocaffeic acid; tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

With potassium carbonate; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.5h;

DOI:10.1016/j.ejmech.2014.11.055

Reference yield:

caffeic acid (331-39-5,501-16-6) → 3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid (116511-71-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 14 h / 20 °C

1.2: 2 h / 20 °C

2.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3 h

With 5%-palladium/activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate;

DOI:10.1002/cmdc.201402292

upstream raw materials:

dihydrocaffeic acid

tert-butyldimethylsilyl chloride

(E)-3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid

caffeic acid

Downstream raw materials:

(-)-<5(S),7(R)>-7-<5-(oct-2-enolide)-3',4'-bis-(t-butyldimethylsilyloxy)>-dihydrocinnamate

3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl ester

(R)-1-methyl-2-[(S)-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl 3-(3,4-dihydroxyphenyl)propanoate

(R)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)propan-2-yl 3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)propanoate