Benzoic acid,2,4-dihydroxy-6-pentadecyl-, 4-carboxy-3-hydroxy-5-methylphenyl ester

Base Information

• Chemical Name: Benzoic acid,2,4-dihydroxy-6-pentadecyl-, 4-carboxy-3-hydroxy-5-methylphenyl ester
• CAS No.: 160219-85-2
• Molecular Formula: C30H42 O7
• Molecular Weight: 514.659
• Mol file: 160219-85-2.mol

Synonyms:AquastatinB

Chemical Property of Benzoic acid,2,4-dihydroxy-6-pentadecyl-, 4-carboxy-3-hydroxy-5-methylphenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzoic acid,2,4-dihydroxy-6-pentadecyl-, 4-carboxy-3-hydroxy-5-methylphenyl ester

There total 13 articles about Benzoic acid,2,4-dihydroxy-6-pentadecyl-, 4-carboxy-3-hydroxy-5-methylphenyl 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: 100.0%

benzyl 4'-(2,4-dibenzyloxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoate (869996-10-1) → 4'-(2,4-dihydroxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoic acid (160219-85-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 96h; under 760 Torr;

DOI:10.1021/jo051384k

Reference yield:

2,4-bis(benzyloxy)-6-pentadecanylbenzoic acid (869996-09-8) → 4'-(2,4-dihydroxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoic acid (160219-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / (CF₃CO)2O / toluene / 2 h / 20 °C

2: 100 percent / H₂ / Pd/C / ethyl acetate / 96 h / 20 °C / 760 Torr

With hydrogen; trifluoroacetic anhydride; palladium on activated charcoal; In ethyl acetate; toluene;

DOI:10.1021/jo051384k

Reference yield:

2,4-bis-benzyloxy-6-pentadecyl-benzoic acid ethyl ester (869996-08-7) → 4'-(2,4-dihydroxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoic acid (160219-85-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.40 g / KOH / dimethylsulfoxide; H₂O / 24 h / 90 °C

2: 94 percent / (CF₃CO)2O / toluene / 2 h / 20 °C

3: 100 percent / H₂ / Pd/C / ethyl acetate / 96 h / 20 °C / 760 Torr

With potassium hydroxide; hydrogen; trifluoroacetic anhydride; palladium on activated charcoal; In water; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1021/jo051384k

upstream raw materials:

benzyl 4'-(2,4-dibenzyloxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoate

2,4-bis(benzyloxy)-6-pentadecanylbenzoic acid

2,4-bis-benzyloxy-6-pentadecyl-benzoic acid ethyl ester

orcinol

Downstream raw materials:

benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate

benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoate

benzyl 4'-(2,4-dihydroxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoate

Refernces

• 1、 Wang, Ping,Zhang, Zhaojun,Yu, Biao. "Total synthesis of CRM646-A and -B, two fungal glucuronides with potent heparinase inhibition activities". . p. 8884 - 8889. Retrieved 2007/10/03.