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

Base Information

• Chemical Name: methyl {3-[5-(3-bromopropionyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate
• CAS No.: 508209-69-6
• Molecular Formula: C₃₂H₃₅BrO₁₃
• Molecular Weight: 707.526
• Mol file: 508209-69-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about methyl {3-[5-(3-bromopropionyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate 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: 93.0%

3-Bromopropionyl chloride (15486-96-1) + methyl 3-<2-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy>phenyl>phenylacetate (173204-11-0) → methyl {3-[5-(3-bromopropionyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate (508209-69-6)

Guidance literature:

With aluminium trichloride; In dichloromethane; at 0 ℃; for 1h;

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

Reference yield:

3-Bromophenylacetic acid (1878-67-7) → methyl {3-[5-(3-bromopropionyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate (508209-69-6)

Guidance literature:

Multi-step reaction with 5 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

With aluminium trichloride; boron tribromide; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; boron trifluoride diethyl etherate; In dichloromethane; water; 1,2-dichloro-ethane; toluene; 5: Friedel-Crafts acylation;

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

Reference yield:

2-Methoxyphenylboronic acid (5720-06-9) → methyl {3-[5-(3-bromopropionyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate (508209-69-6)

Guidance literature:

Multi-step reaction with 4 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

With aluminium trichloride; boron tribromide; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; In dichloromethane; water; 1,2-dichloro-ethane; toluene; 4: Friedel-Crafts acylation;

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

upstream raw materials:

3-Bromopropionyl chloride

methyl 3-<2-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy>phenyl>phenylacetate

3-Bromophenylacetic acid

2-Methoxyphenylboronic acid

Downstream raw materials:

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

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

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

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