3,5-dibenzyloxy-4-(2-benzyloxycarbonyl-1-naphthylcarbonyl)benzoic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: 3,5-dibenzyloxy-4-(2-benzyloxycarbonyl-1-naphthylcarbonyl)benzoic acid 1,1-dimethylethyl ester
• CAS No.: 167832-48-6
• Molecular Formula: C₄₄H₃₈O₇
• Molecular Weight: 678.782
• Mol file: 167832-48-6.mol

Synonyms:3,5-dibenzyloxy-4-(2-benzyloxycarbonyl-1-naphthylcarbonyl)benzoic acid 1,1-dimethylethyl ester

Chemical Property of 3,5-dibenzyloxy-4-(2-benzyloxycarbonyl-1-naphthylcarbonyl)benzoic acid 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-dibenzyloxy-4-(2-benzyloxycarbonyl-1-naphthylcarbonyl)benzoic acid 1,1-dimethylethyl ester

There total 6 articles about 3,5-dibenzyloxy-4-(2-benzyloxycarbonyl-1-naphthylcarbonyl)benzoic acid 1,1-dimethylethyl 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: 73.0%

benzyl bromide (100-39-0) + 1-(2,6-bis-benzyloxy-4-tert-butoxycarbonyl-benzoyl)-naphthalene-2-carboxylic acid (167832-47-5) → 3,5-dibenzyloxy-4-(2-benzyloxycarbonyl-1-naphthylcarbonyl)benzoic acid 1,1-dimethylethyl ester (167832-48-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm020018f

Reference yield:

3,5-Bis-benzyloxy-4-chlorocarbonyl-benzoic acid tert-butyl ester (158980-58-6) → 3,5-dibenzyloxy-4-(2-benzyloxycarbonyl-1-naphthylcarbonyl)benzoic acid 1,1-dimethylethyl ester (167832-48-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 51 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

2: 52 percent / n-BuLi / tetrahydrofuran; hexane / 2.5 h / -78 °C

3: 35 percent / KBr; aq. NaHCO₃; NaOCl / TEMPO / CH₂Cl₂ / 2 h / 0 °C

4: 99 percent / aq. sulfamic acid; NaClO₂ / acetonitrile / 1 h / 20 °C

5: 73 percent / K₂CO₃ / dimethylformamide / 20 °C

With dmap; sodium hypochlorite; sodium chlorite; n-butyllithium; aminosulfonic acid; sodium hydrogencarbonate; potassium carbonate; triethylamine; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm020018f

Reference yield:

2,6-bis(benzyloxy)-4-<(1,1-dimethylethoxy)carbonyl>benzoic acid (158980-56-4) → 3,5-dibenzyloxy-4-(2-benzyloxycarbonyl-1-naphthylcarbonyl)benzoic acid 1,1-dimethylethyl ester (167832-48-6)

Guidance literature:

Multi-step reaction with 6 steps

1: oxalyl chloride / CH₂Cl₂; dimethylformamide / 3 h / 20 °C

2: 51 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

3: 52 percent / n-BuLi / tetrahydrofuran; hexane / 2.5 h / -78 °C

4: 35 percent / KBr; aq. NaHCO₃; NaOCl / TEMPO / CH₂Cl₂ / 2 h / 0 °C

5: 99 percent / aq. sulfamic acid; NaClO₂ / acetonitrile / 1 h / 20 °C

6: 73 percent / K₂CO₃ / dimethylformamide / 20 °C

With dmap; sodium hypochlorite; sodium chlorite; n-butyllithium; oxalyl dichloride; aminosulfonic acid; sodium hydrogencarbonate; potassium carbonate; triethylamine; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm020018f

upstream raw materials:

benzyl bromide

1-(2,6-bis-benzyloxy-4-tert-butoxycarbonyl-benzoyl)-naphthalene-2-carboxylic acid

2,6-bis(benzyloxy)-4-<(1,1-dimethylethoxy)carbonyl>benzoic acid

3,5-Bis-benzyloxy-4-chlorocarbonyl-benzoic acid tert-butyl ester

Downstream raw materials:

3,5-dibenzyloxy-4-(2-benzyloxycarbonyl-1-naphthylcarbonyl)benzoic acid