4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Base Information

• Chemical Name: 4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
• CAS No.: 303127-82-4
• Molecular Formula: C₃₄H₃₂O₈
• Molecular Weight: 568.623
• Mol file: 303127-82-4.mol

Synonyms:4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Chemical Property of 4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

There total 5 articles about 4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 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: 83.0%

benzoyl chloride (98-88-4) + p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside (303127-81-3) → 4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (303127-82-4)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; for 1.5h;

DOI:10.1039/b002835p

Reference yield:

4-methoxy-phenol (150-76-5) → 4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (303127-82-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / trimethylsilyl triflate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

2: 89 percent / methanol / 16 h / 20 °C

3: 84 percent / CF₃CO₂H / 0.33 h

4: 83 percent / pyridine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trifluoroacetic acid; In methanol; dichloromethane; 1: Etherification / 2: Deacetylation / 3: Cyclization / 4: Acylation;

DOI:10.1039/b002835p

Reference yield:

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9) → 4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (303127-82-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / trimethylsilyl triflate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

2: 89 percent / methanol / 16 h / 20 °C

3: 84 percent / CF₃CO₂H / 0.33 h

4: 83 percent / pyridine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trifluoroacetic acid; In methanol; dichloromethane; 1: Etherification / 2: Deacetylation / 3: Cyclization / 4: Acylation;

DOI:10.1039/b002835p

upstream raw materials:

benzoyl chloride

p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside

4-methoxy-phenol

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

Downstream raw materials:

4-Methoxyphenyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranoside

Methyl (4-methoxyphenyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosid)uronate

(2S,3S,4S,5R,6S)-5-Benzoyloxy-3,4-bis-benzyloxy-6-(4-methoxy-phenoxy)-tetrahydro-pyran-2-carboxylic acid

Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano