(2S,3S)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate

Base Information

• Chemical Name: (2S,3S)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate
• CAS No.: 1283147-57-8
• Molecular Formula: C₂₅H₂₉NO₇
• Molecular Weight: 455.508
• Mol file: 1283147-57-8.mol

Synonyms:(2S,3S)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate

Chemical Property of (2S,3S)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate

There total 9 articles about (2S,3S)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate 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: 87.0%

(R)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-diazo-2-(2-(3,4-dimethoxybenzyloxy)-3-methoxyphenyl)acetate (1283147-54-5) → (2S,3S)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate (1283147-57-8) + (2R,3R)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate

Guidance literature:

With Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; In dichloromethane; at 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ja2010225

Reference yield:

(R)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-(2-(benzyloxy)-3-methoxyphenyl)acetate (1283147-55-6) → (2S,3S)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate (1283147-57-8) + (2R,3R)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate

Guidance literature:

Multi-step reaction with 4 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere

2: potassium carbonate / acetone / Inert atmosphere; Reflux

3: 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 0 - 20 °C / Inert atmosphere

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

With Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; palladium 10% on activated carbon; 4-acetamidobenzenesulfonyl azide; hydrogen; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; acetone; acetonitrile;

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)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate (1283147-57-8) + (2R,3R)-[(R)-1-oxo-1-(Pyrrolidin-1-yl)propan-2-yl] 2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate

Guidance literature:

Multi-step reaction with 3 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

With Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; 4-acetamidobenzenesulfonyl azide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetone; acetonitrile;

DOI:10.1021/ja2010225

upstream raw materials:

(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

(R)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-diazo-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

(2S,3S)-2-(3,4-Dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid

(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