p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside

Base Information

• Chemical Name: p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside
• CAS No.: 1262589-19-4
• Molecular Formula: C₅₆H₅₄O₁₅
• Molecular Weight: 967.036
• Mol file: 1262589-19-4.mol

Synonyms:p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside

Chemical Property of p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside

There total 5 articles about p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 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%

p-methoxyphenyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside (1104513-35-0) + p-methylphenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside (323195-40-0) → p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside (1262589-19-4)

Guidance literature:

p-methoxyphenyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside; p-methylphenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside; With N-iodo-succinimide; In dichloromethane; at 0 ℃; for 0.666667h; Molecular sieve; Inert atmosphere;

With lanthanum(lll) triflate; In dichloromethane; at 0 ℃; for 0.333333h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2014.05.018

Reference yield:

benzyl bromide (100-39-0) → p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside (1262589-19-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h

2.1: acetic acid / water / 2 h / 80 °C

3.1: camphor-10-sulfonic acid / acetonitrile / 0.5 h / 20 °C

4.1: N-iodo-succinimide / dichloromethane / 0.67 h / 0 °C / Molecular sieve; Inert atmosphere

4.2: 0.33 h / 0 °C / Molecular sieve; Inert atmosphere

With N-iodo-succinimide; camphor-10-sulfonic acid; sodium hydride; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1016/j.carres.2014.05.018

Reference yield:

4-methoxyphenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside (159922-68-6) → p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside (1262589-19-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid / water / 2 h / 80 °C

2.1: camphor-10-sulfonic acid / acetonitrile / 0.5 h / 20 °C

3.1: N-iodo-succinimide / dichloromethane / 0.67 h / 0 °C / Molecular sieve; Inert atmosphere

3.2: 0.33 h / 0 °C / Molecular sieve; Inert atmosphere

With N-iodo-succinimide; camphor-10-sulfonic acid; acetic acid; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.carres.2014.05.018

upstream raw materials:

benzyl bromide

4-methoxyphenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside

4-methoxyphenyl 2,6-di-O-benzyl-β-D-galactopyranoside

p-methoxyphenyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside

Downstream raw materials:

p-methoxyphenyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-glucopyranosyl-(1 → 3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside