methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate

Base Information

• Chemical Name: methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate
• CAS No.: 223930-86-7
• Molecular Formula: C₃₁H₃₆O₁₃
• Molecular Weight: 616.619
• Mol file: 223930-86-7.mol

Synonyms:methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate

Chemical Property of methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate

There total 4 articles about methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate 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: 67.0%

(+/-)-methyl 3-p-benzyloxyphenyl-2-hydroxypropionate (128316-64-3,481072-37-1) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate (223930-86-7)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate;

DOI:10.1016/S0040-4039(99)00602-4

Reference yield:

4-hydroxyphenylpiruvic acid (156-39-8) → methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate (223930-86-7)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol; benzene / 20 °C

2: H₂ / Pd/C / methanol / 10 h / 20 °C

3: 73 percent / K₂CO₃ / dimethylformamide / 20 °C

4: 67 percent / AgOTf / CH₂Cl₂ / 1 h / 0 °C

With hydrogen; silver trifluoromethanesulfonate; potassium carbonate; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Methylation / 2: Catalytic hydrogenation / 3: Alkylation / 4: Substitution;

DOI:10.1016/S0040-4020(99)00618-3

Reference yield:

methyl 2-oxo-3-(4-hydroxyphenyl)propionate (154722-74-4) → methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate (223930-86-7)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/C / methanol / 10 h / 20 °C

2: 73 percent / K₂CO₃ / dimethylformamide / 20 °C

3: 67 percent / AgOTf / CH₂Cl₂ / 1 h / 0 °C

With hydrogen; silver trifluoromethanesulfonate; potassium carbonate; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Catalytic hydrogenation / 2: Alkylation / 3: Substitution;

DOI:10.1016/S0040-4020(99)00618-3

upstream raw materials:

(+/-)-methyl 3-p-benzyloxyphenyl-2-hydroxypropionate

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

4-hydroxyphenylpiruvic acid

methyl 2-oxo-3-(4-hydroxyphenyl)propionate

Downstream raw materials:

(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester

methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylpropionate

methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-propionate