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

Base Information

• Chemical Name: 4-methylphenyl 2-O-acetyl-4-azido-6-O-benzyl-4-deoxy-3-O-(methoxyethanoyl)-1-thio-β-D-galactopyranoside
• CAS No.: 219518-38-4
• Molecular Formula: C₂₅H₂₉N₃O₇S
• Molecular Weight: 515.587
• Mol file: 219518-38-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 4-methylphenyl 2-O-acetyl-4-azido-6-O-benzyl-4-deoxy-3-O-(methoxyethanoyl)-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:

((2S,3R,4R,5R,6R)-3-Acetoxy-6-benzyloxymethyl-2-p-tolylsulfanyl-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-4-yloxy)-acetic acid methyl ester → 4-methylphenyl 2-O-acetyl-4-azido-6-O-benzyl-4-deoxy-3-O-(methoxyethanoyl)-1-thio-β-D-galactopyranoside (219518-38-4)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 22 ℃; for 15h;

DOI:10.1021/jo981204p

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 4-methylphenyl 2-O-acetyl-4-azido-6-O-benzyl-4-deoxy-3-O-(methoxyethanoyl)-1-thio-β-D-galactopyranoside (219518-38-4)

Guidance literature:

Multi-step reaction with 6 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

5: pyridine / CH₂Cl₂ / 3 h / 22 °C

6: 1.76 g / NaN₃ / dimethylformamide / 15 h / 22 °C

With pyridine; hydrogenchloride; dmap; sodium azide; 4 Angstroems MS; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo981204p

Reference yield:

p-methylphenyl 1-thio-β-D-glucopyranoside (1152-39-2) → 4-methylphenyl 2-O-acetyl-4-azido-6-O-benzyl-4-deoxy-3-O-(methoxyethanoyl)-1-thio-β-D-galactopyranoside (219518-38-4)

Guidance literature:

Multi-step reaction with 6 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

5: pyridine / CH₂Cl₂ / 3 h / 22 °C

6: 1.76 g / NaN₃ / dimethylformamide / 15 h / 22 °C

With pyridine; hydrogenchloride; dmap; sodium azide; 4 Angstroems MS; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo981204p

upstream raw materials:

benzaldehyde dimethyl acetal

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

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

4-methylphenyl 4,6-O-benzylidene-3-O-(methoxyethanoyl)-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-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside>

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>