diphenyl (3R,4R)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate

Base Information

• Chemical Name: diphenyl (3R,4R)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate
• CAS No.: 1414851-96-9
• Molecular Formula: C₃₁H₃₀N₃O₇P
• Molecular Weight: 587.569
• Mol file: 1414851-96-9.mol

Synonyms:diphenyl (3R,4R)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate

Chemical Property of diphenyl (3R,4R)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diphenyl (3R,4R)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate

There total 4 articles about diphenyl (3R,4R)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate 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: 64.0%

diphenyl hydrogen phosphite (4712-55-4) + 3-carbobenzyloxy-6-(4-methoxypicolinoyl)-3,6-diazabicyclo[3.1.0]hexane (1414851-50-5) → diphenyl (3R,4R)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate (1414851-96-9)

Guidance literature:

With N-(9-deoxy-epi-cinchonin-9-yl)picolinamide; diethylzinc; sodium carbonate; In toluene; benzene; at 20 ℃; for 64h; enantioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/ja309963w

Reference yield:

2-cyano-4-nitro-pyridine (19235-88-2) → diphenyl (3R,4R)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate (1414851-96-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sulfuric acid / 2 h / 120 °C / Inert atmosphere

1.2: Dowex? (H+ form) / 2 h / 80 °C / Inert atmosphere

2.1: sodium / 2 h / Reflux; Inert atmosphere

2.2: Dowex? / Inert atmosphere

3.1: 1,1'-carbonyldiimidazole / dichloromethane / 40 °C / Inert atmosphere

3.2: 3 h / 0 - 23 °C / Inert atmosphere

4.1: N-(9-deoxy-epi-cinchonin-9-yl)picolinamide; sodium carbonate; diethylzinc / toluene; benzene / 64 h / 20 °C / Molecular sieve; Inert atmosphere

With sulfuric acid; N-(9-deoxy-epi-cinchonin-9-yl)picolinamide; diethylzinc; sodium; sodium carbonate; 1,1'-carbonyldiimidazole; In dichloromethane; toluene; benzene;

DOI:10.1021/ja309963w

Reference yield:

4-nitraminopyridine N-oxide (1124-33-0) → diphenyl (3R,4R)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate (1414851-96-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dimethyl sulfate / water / 2 h / -8 - 70 °C / Inert atmosphere

1.2: 12 h / Inert atmosphere

2.1: sulfuric acid / 2 h / 120 °C / Inert atmosphere

2.2: Dowex? (H+ form) / 2 h / 80 °C / Inert atmosphere

3.1: sodium / 2 h / Reflux; Inert atmosphere

3.2: Dowex? / Inert atmosphere

4.1: 1,1'-carbonyldiimidazole / dichloromethane / 40 °C / Inert atmosphere

4.2: 3 h / 0 - 23 °C / Inert atmosphere

5.1: N-(9-deoxy-epi-cinchonin-9-yl)picolinamide; sodium carbonate; diethylzinc / toluene; benzene / 64 h / 20 °C / Molecular sieve; Inert atmosphere

With sulfuric acid; N-(9-deoxy-epi-cinchonin-9-yl)picolinamide; diethylzinc; sodium; sodium carbonate; dimethyl sulfate; 1,1'-carbonyldiimidazole; In dichloromethane; water; toluene; benzene;

DOI:10.1021/ja309963w

upstream raw materials:

2-cyano-4-nitro-pyridine

diphenyl hydrogen phosphite

3-carbobenzyloxy-6-(4-methoxypicolinoyl)-3,6-diazabicyclo[3.1.0]hexane

4-methoxypyridine-2-carboxylic acid

Refernces