3-(4-Hydroxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

Base Information

• Chemical Name: 3-(4-Hydroxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester
• CAS No.: 128316-67-6
• Molecular Formula: C₂₄H₃₀O₁₃
• Molecular Weight: 526.494
• Mol file: 128316-67-6.mol

Synonyms:

Chemical Property of 3-(4-Hydroxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-Hydroxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

There total 2 articles about 3-(4-Hydroxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester 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:

3-(4-Benzyloxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (128316-65-4,128316-66-5) → 3-(4-Hydroxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (128316-67-6,128316-68-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; for 8h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(01)93902-4

Reference yield:

(+/-)-methyl 3-p-benzyloxyphenyl-2-hydroxypropionate (128316-64-3,481072-37-1) → 3-(4-Hydroxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (128316-67-6,128316-68-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / AgOTf, molecular sieves 4A / CH₂Cl₂ / 0.33 h / 0 °C

2: H₂ / Pd/C / methanol; ethyl acetate / 8 h / Ambient temperature

With 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(01)93902-4

Reference yield:

3-(4-Hydroxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (128316-67-6,128316-68-7) → potassium lespedezate (123955-02-2)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / Ambient temperature

2: 80 percent / DDQ / toluene / 120 h / Heating

3: nBu₄NF / tetrahydrofuran / 1 h / 0 °C

4: 4 percent / KOH / methanol / 0.5 h / 0 °C

With 1H-imidazole; potassium hydroxide; tetrabutyl ammonium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(01)93902-4

upstream raw materials:

3-(4-Benzyloxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

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

Downstream raw materials:

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

potassium isolespedezate

potassium lespedezate

(Z)-3-(4-Hydroxy-phenyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester