4-methylphenyl 2-O-acetyl-6-O-benzyl-3-O-(methoxyethanoyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: 4-methylphenyl 2-O-acetyl-6-O-benzyl-3-O-(methoxyethanoyl)-1-thio-β-D-glucopyranoside
• CAS No.: 219518-36-2
• Molecular Formula: C₂₅H₃₀O₈S
• Molecular Weight: 490.574
• Mol file: 219518-36-2.mol

Synonyms:4-methylphenyl 2-O-acetyl-6-O-benzyl-3-O-(methoxyethanoyl)-1-thio-β-D-glucopyranoside

Chemical Property of 4-methylphenyl 2-O-acetyl-6-O-benzyl-3-O-(methoxyethanoyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methylphenyl 2-O-acetyl-6-O-benzyl-3-O-(methoxyethanoyl)-1-thio-β-D-glucopyranoside

There total 5 articles about 4-methylphenyl 2-O-acetyl-6-O-benzyl-3-O-(methoxyethanoyl)-1-thio-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: 80.0%

4-methylphenyl 2-O-acetyl-4,6-O-benzylidene-3-O-(methoxyethanoyl)-1-thio-β-D-glucopyranoside (219518-34-0) → 4-methylphenyl 2-O-acetyl-6-O-benzyl-3-O-(methoxyethanoyl)-1-thio-β-D-glucopyranoside (219518-36-2)

Guidance literature:

With hydrogenchloride; 4 Angstroems MS; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 1.5h;

DOI:10.1021/jo981204p

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 4-methylphenyl 2-O-acetyl-6-O-benzyl-3-O-(methoxyethanoyl)-1-thio-β-D-glucopyranoside (219518-36-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / TsOH / acetonitrile / 17 h

3: 98 percent / DMAP / pyridine / 0.67 h / 22 °C

4: 80 percent / NaBH₃CN, 4 Angstroems MS, HCl / tetrahydrofuran; diethyl ether / 1.5 h / 0 °C

With hydrogenchloride; dmap; 4 Angstroems MS; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; diethyl ether; acetonitrile;

DOI:10.1021/jo981204p

Reference yield:

p-methylphenyl 1-thio-β-D-glucopyranoside (1152-39-2) → 4-methylphenyl 2-O-acetyl-6-O-benzyl-3-O-(methoxyethanoyl)-1-thio-β-D-glucopyranoside (219518-36-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / TsOH / acetonitrile / 17 h

3: 98 percent / DMAP / pyridine / 0.67 h / 22 °C

4: 80 percent / NaBH₃CN, 4 Angstroems MS, HCl / tetrahydrofuran; diethyl ether / 1.5 h / 0 °C

With hydrogenchloride; dmap; 4 Angstroems MS; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; diethyl ether; acetonitrile;

DOI:10.1021/jo981204p

upstream raw materials:

4-methylphenyl 2-O-acetyl-4,6-O-benzylidene-3-O-(methoxyethanoyl)-1-thio-β-D-glucopyranoside

benzaldehyde dimethyl acetal

p-methylphenyl 1-thio-β-D-glucopyranoside

4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Downstream raw materials:

4-methylphenyl <2-O-acetyl-4-azido-6-O-benzyl-4-deoxy-3-O-(methoxyethanoyl)-β-D-galactopyranosyl>-(1->4)-<2-deoxy-6-O-benzyl-2-(tetrachlorophthalimido)-β-D-glucopyranoside>

4-methylphenyl <2-O-acetyl-4-azido-6-O-benzyl-4-deoxy-3-O-(methoxyethanoyl)-β-D-galactopyranosyl>-(1->4)-<2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside>

4-methylphenyl 2-O-acetyl-4-azido-6-O-benzyl-4-deoxy-3-O-(methoxyethanoyl)-1-thio-β-D-galactopyranoside