{3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic acid

Base Information

• Chemical Name: {3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic acid
• CAS No.: 724700-58-7
• Molecular Formula: C₂₃H₂₉NO₈
• Molecular Weight: 447.485
• Mol file: 724700-58-7.mol

Synonyms:{3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic acid

Chemical Property of {3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic acid

There total 14 articles about {3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic 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: 78.0%

methyl {3-[5-(3-aminopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate (508209-72-1) → {3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic acid (724700-58-7)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 24h;

DOI:10.1002/1099-0690(200212)2002:23<3966::AID-EJOC3966>3.0.CO;2-P

Reference yield:

3-Bromophenylacetic acid (1878-67-7) → {3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic acid (724700-58-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / H₂SO₄ / Heating

2: 96 percent / Na₂CO₃ / Pd(PPh₃)4 / toluene; H₂O / 16 h / Heating

3: 60 percent / BBr₃ / CH₂Cl₂ / 10 h / -10 °C

4: BF₃*Et₂O / 1,2-dichloro-ethane / 24 h / 20 °C

5: 93 percent / AlCl₃ / CH₂Cl₂ / 1 h / 0 °C

6: 69 percent / BH₃*THF / 3 h / 20 °C

7: 56 percent / K₂CO₃ / dimethylformamide / 2 h / 95 °C

8: aq. NaOH / 22 h / Heating

With sodium hydroxide; aluminium trichloride; borane-THF; boron tribromide; sodium carbonate; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; boron trifluoride diethyl etherate; In dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 5: Friedel-Crafts acylation / 7: Gabriel synthesis / 8: Gabriel synthesis;

DOI:10.1002/1099-0690(200212)2002:23<3966::AID-EJOC3966>3.0.CO;2-P

Reference yield:

2-Methoxyphenylboronic acid (5720-06-9) → {3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic acid (724700-58-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / Na₂CO₃ / Pd(PPh₃)4 / toluene; H₂O / 16 h / Heating

2: 60 percent / BBr₃ / CH₂Cl₂ / 10 h / -10 °C

3: BF₃*Et₂O / 1,2-dichloro-ethane / 24 h / 20 °C

4: 93 percent / AlCl₃ / CH₂Cl₂ / 1 h / 0 °C

5: 69 percent / BH₃*THF / 3 h / 20 °C

6: 56 percent / K₂CO₃ / dimethylformamide / 2 h / 95 °C

7: aq. NaOH / 22 h / Heating

With sodium hydroxide; aluminium trichloride; borane-THF; boron tribromide; sodium carbonate; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; In dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 4: Friedel-Crafts acylation / 6: Gabriel synthesis / 7: Gabriel synthesis;

DOI:10.1002/1099-0690(200212)2002:23<3966::AID-EJOC3966>3.0.CO;2-P

upstream raw materials:

methyl {3-[5-(3-aminopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate

methyl 3-[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-5-(3-phthalimidylpropyl)phenyl]phenylacetate

3-Bromophenylacetic acid

2-Methoxyphenylboronic acid