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

Base Information

• Chemical Name: methyl 3-[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-5-(3-phthalimidylpropyl)phenyl]phenylacetate
• CAS No.: 508209-77-6
• Molecular Formula: C₄₀H₄₁NO₁₄
• Molecular Weight: 759.764

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

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

Chemical Property:

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

There total 11 articles about methyl 3-[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-5-(3-phthalimidylpropyl)phenyl]phenylacetate 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: 56.0%

phthalimide (136918-14-4,85-41-6) + methyl {3-[5-(3-bromopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate (508209-70-9) → methyl 3-[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-5-(3-phthalimidylpropyl)phenyl]phenylacetate (508209-77-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 95 ℃; for 2h;

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-[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-5-(3-phthalimidylpropyl)phenyl]phenylacetate (508209-77-6)

Guidance literature:

Multi-step reaction with 7 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

With 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;

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-[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-5-(3-phthalimidylpropyl)phenyl]phenylacetate (508209-77-6)

Guidance literature:

Multi-step reaction with 6 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

With 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;

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

upstream raw materials:

phthalimide

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

3-Bromophenylacetic acid

2-Methoxyphenylboronic acid

Downstream raw materials:

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

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