p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
• CAS No.: 220645-60-3
• Molecular Formula: C₂₇H₂₈O₅S
• Molecular Weight: 464.582

Synonyms:p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Chemical Property of p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Chemical Property:

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Technology Process of p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

There total 5 articles about p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-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: 31.4%

benzyl bromide (100-39-0) + p-methylphenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-86-3) → p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-60-3) + p-methylphenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-87-4) + p-methylphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Guidance literature:

With sodium hydroxide; teterabutylammonium; sulfuric acid; In dichloromethane; for 20h; Heating;

DOI:10.1021/ja982232s

Reference yield:

p-methylphenyl-1-thio-β-D-galactopyranoside (1152-39-2,28244-98-6,121523-95-3,131488-68-1) → p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / camphorsulfonic acid / acetonitrile / 2 h / Ambient temperature

2: 31.4 percent / 1.0 M aq. NaOH, Bu₄N/HSO₄ / CH₂Cl₂ / 20 h / Heating

With sodium hydroxide; teterabutylammonium; sulfuric acid; camphor-10-sulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1021/ja982232s

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / camphorsulfonic acid / acetonitrile / 2 h / Ambient temperature

2: 31.4 percent / 1.0 M aq. NaOH, Bu₄N/HSO₄ / CH₂Cl₂ / 20 h / Heating

With sodium hydroxide; teterabutylammonium; sulfuric acid; camphor-10-sulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1021/ja982232s

upstream raw materials:

benzyl bromide

p-methylphenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside

p-methylphenyl-1-thio-β-D-galactopyranoside

benzaldehyde dimethyl acetal

Downstream raw materials:

p-tolyl 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl-α(1→3)-4,6-O-benzylidene-2-O-benzyl-thio-β-D-galactopyranoside

methyl 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl-α(1→3)-4,6-O-benzylidene-2-O-benzyl-D-galactopyranosyl-α(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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