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

Base Information

• Chemical Name: 1-(2,6-bis-benzyloxy-4-tert-butoxycarbonyl-benzoyl)-naphthalene-2-carboxylic acid
• CAS No.: 167832-47-5
• Molecular Formula: C₃₇H₃₂O₇
• Molecular Weight: 588.657
• Mol file: 167832-47-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 1-(2,6-bis-benzyloxy-4-tert-butoxycarbonyl-benzoyl)-naphthalene-2-carboxylic 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%

3,5-dibenzyloxy-4-(2-formyl-1-naphthylcarbonyl)benzoic acid 1,1-dimethylethyl ester (167832-46-4) → 1-(2,6-bis-benzyloxy-4-tert-butoxycarbonyl-benzoyl)-naphthalene-2-carboxylic acid (167832-47-5)

Guidance literature:

With sodium chlorite; aminosulfonic acid; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/jm020018f

Reference yield:

2,6-bis(benzyloxy)-4-<(1,1-dimethylethoxy)carbonyl>benzoic acid (158980-56-4) → 1-(2,6-bis-benzyloxy-4-tert-butoxycarbonyl-benzoyl)-naphthalene-2-carboxylic acid (167832-47-5)

Guidance literature:

Multi-step reaction with 5 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

With dmap; sodium hypochlorite; sodium chlorite; n-butyllithium; oxalyl dichloride; aminosulfonic acid; sodium hydrogencarbonate; 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:

3,5-Bis-benzyloxy-4-chlorocarbonyl-benzoic acid tert-butyl ester (158980-58-6) → 1-(2,6-bis-benzyloxy-4-tert-butoxycarbonyl-benzoyl)-naphthalene-2-carboxylic acid (167832-47-5)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jm020018f

upstream raw materials:

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

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

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

3,5-dibenzyloxy-4-[2-(hydroxymethyl)-1-naphthylcarbonyl]benzoic acid 1,1-dimethylethyl ester

Downstream raw materials:

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

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