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

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Chemical Name:diphenyl (3S,4S)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate
CAS No.:1426583-26-7
Molecular Formula:C₃₁H₃₀N₃O₇P
Molecular Weight:587.569
Hs Code.:

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

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

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

There total 4 articles about diphenyl (3S,4S)-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: 65.0%

: 4712-55-4
diphenyl hydrogen phosphite

: 1414851-50-5
3-carbobenzyloxy-6-(4-methoxypicolinoyl)-3,6-diazabicyclo[3.1.0]hexane

: 1426583-26-7
diphenyl (3S,4S)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate

Guidance literature:: With N-(9-deoxy-epi-cinchonidin-9-yl)picolinamide; diethylzinc; sodium carbonate; In toluene; benzene; at 20 ℃; for 42h; enantioselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1021/ja309963w

Reference yield:

: 19235-88-2
2-cyano-4-nitro-pyridine

: 1426583-26-7
diphenyl (3S,4S)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate

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-cinchonidin-9-yl)picolinamide; sodium carbonate; diethylzinc / toluene; benzene / 42 h / 20 °C / Molecular sieve; Inert atmosphere

With sulfuric acid; N-(9-deoxy-epi-cinchonidin-9-yl)picolinamide; diethylzinc; sodium; sodium carbonate; 1,1'-carbonyldiimidazole; In dichloromethane; toluene; benzene;
DOI:10.1021/ja309963w

Reference yield:

: 1124-33-0
4-nitraminopyridine N-oxide

: 1426583-26-7
diphenyl (3S,4S)-1-(benzyloxycarbonyl)-4-(4-methoxypicolinamido)pyrrolidin-3-ylphosphonate

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-cinchonidin-9-yl)picolinamide; sodium carbonate; diethylzinc / toluene; benzene / 42 h / 20 °C / Molecular sieve; Inert atmosphere

With sulfuric acid; N-(9-deoxy-epi-cinchonidin-9-yl)picolinamide; diethylzinc; sodium; sodium carbonate; dimethyl sulfate; 1,1'-carbonyldiimidazole; In dichloromethane; water; toluene; benzene;
DOI:10.1021/ja309963w