(2S,3S)-2-(3,4-dimethoxyphenyl)-4-{(E)-3-[(R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yloxy]-3-oxoprop-1-eny}-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid

Base Information

• Chemical Name: (2S,3S)-2-(3,4-dimethoxyphenyl)-4-{(E)-3-[(R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yloxy]-3-oxoprop-1-eny}-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid
• CAS No.: 1283147-51-2
• Molecular Formula: C₃₃H₃₄O₁₂
• Molecular Weight: 622.626
• Mol file: 1283147-51-2.mol

Synonyms:(2S,3S)-2-(3,4-dimethoxyphenyl)-4-{(E)-3-[(R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yloxy]-3-oxoprop-1-eny}-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid

Chemical Property of (2S,3S)-2-(3,4-dimethoxyphenyl)-4-{(E)-3-[(R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yloxy]-3-oxoprop-1-eny}-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(3,4-dimethoxyphenyl)-4-{(E)-3-[(R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yloxy]-3-oxoprop-1-eny}-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid

There total 12 articles about (2S,3S)-2-(3,4-dimethoxyphenyl)-4-{(E)-3-[(R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yloxy]-3-oxoprop-1-eny}-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid 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: 93.0%

(R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yl acrylate + (2S,3S)-2-(3,4-Dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid (1283147-53-4) → (2S,3S)-2-(3,4-dimethoxyphenyl)-4-{(E)-3-[(R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yloxy]-3-oxoprop-1-eny}-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid (1283147-51-2)

Guidance literature:

With (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen; palladium diacetate; potassium hydrogencarbonate; In tert-Amyl alcohol; at 85 ℃; for 2h; under 760.051 Torr;

DOI:10.1021/ja2010225

Reference yield:

(-)-(R)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate (457893-80-0) → (2S,3S)-2-(3,4-dimethoxyphenyl)-4-{(E)-3-[(R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yloxy]-3-oxoprop-1-eny}-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid (1283147-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C / Inert atmosphere

2: (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen; palladium diacetate; potassium hydrogencarbonate / tert-Amyl alcohol / 2 h / 85 °C / 760.05 Torr

With dmap; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen; palladium diacetate; potassium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tert-Amyl alcohol; dichloromethane;

DOI:10.1021/ja2010225

Reference yield:

(R)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-(2-(benzyloxy)-3-methoxyphenyl)acetate (1283147-58-9) → (2S,3S)-2-(3,4-dimethoxyphenyl)-4-{(E)-3-[(R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yloxy]-3-oxoprop-1-eny}-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid (1283147-51-2)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / acetone / Inert atmosphere; Reflux

2: 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 0 - 20 °C / Inert atmosphere

3: Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 / dichloromethane / 20 °C / Inert atmosphere

4: barium hydroxide octahydrate / tetrahydrofuran; methanol / 0 - 20 °C / Inert atmosphere

5: (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen; palladium diacetate; potassium hydrogencarbonate / tert-Amyl alcohol / 2 h / 85 °C / 760.05 Torr

With barium hydroxide octahydrate; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; 4-acetamidobenzenesulfonyl azide; oxygen; palladium diacetate; potassium carbonate; potassium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; tert-Amyl alcohol; dichloromethane; acetone; acetonitrile;

DOI:10.1021/ja2010225

upstream raw materials:

(-)-(R)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

(R)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-(2-(benzyloxy)-3-methoxyphenyl)acetate

(R)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-(2-(benzyloxy)-3-methoxyphenyl)acetate

(R)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-(2-(3,4-dimethoxybenzyloxy)-3-methoxyphenyl)acetate

Downstream raw materials:

(2S,3S)-4-((E)-3-((R)-1-carboxy-2-(3,4-dimethoxyphenyl)ethoxy)-3-oxoprop-1-en-1-yl)-2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid

(2S,3S)-methyl 2-(3,4-dimethoxyphenyl)-4-((E)-3-(((R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yl)oxy)-3-oxoprop-1-en-1-yl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate