(R)-(+)-4-(diethoxyphosphoryloxy)-5-(dimethoxyphosphoryl)-2-phenyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

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Chemical Name:(R)-(+)-4-(diethoxyphosphoryloxy)-5-(dimethoxyphosphoryl)-2-phenyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester
CAS No.:814256-52-5
Molecular Formula:C₂₁H₃₃NO₉P₂
Molecular Weight:505.442
Hs Code.:

Synonyms:(R)-(+)-4-(diethoxyphosphoryloxy)-5-(dimethoxyphosphoryl)-2-phenyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

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Chemical Property of (R)-(+)-4-(diethoxyphosphoryloxy)-5-(dimethoxyphosphoryl)-2-phenyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

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Technology Process of (R)-(+)-4-(diethoxyphosphoryloxy)-5-(dimethoxyphosphoryl)-2-phenyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

There total 6 articles about (R)-(+)-4-(diethoxyphosphoryloxy)-5-(dimethoxyphosphoryl)-2-phenyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl 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: 81.0%

: 814-49-3
diethyl chlorophosphate

: dimethyl (5R)-N-(tert-butoxycarbonyl)-3-oxo-5-phenylpyrrolidine-2-phosphonate

: 814256-52-5
(R)-(+)-4-(diethoxyphosphoryloxy)-5-(dimethoxyphosphoryl)-2-phenyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

Guidance literature:: dimethyl (5R)-N-(tert-butoxycarbonyl)-3-oxo-5-phenylpyrrolidine-2-phosphonate; With 18-crown-6 ether; sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

diethyl chlorophosphate; In tetrahydrofuran; for 0.5h;
DOI:10.1021/ol048157+

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 814256-52-5
(R)-(+)-4-(diethoxyphosphoryloxy)-5-(dimethoxyphosphoryl)-2-phenyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: TFA / methanol / 0 - 20 °C

1.2: 90 percent / NEt₃; DMAP / tetrahydrofuran / 3 h / 0 °C

2.1: 83 percent / NaH; 4-acetamidobenzenesulfonyl azide / tetrahydrofuran / 1 h / 20 °C

3.1: 78 percent / rhodium(II) acetate dimer / CH₂Cl₂ / 16 h / 35 °C

4.1: NaH; 18-crown-6 / tetrahydrofuran / 0.08 h / 20 °C

4.2: 81 percent / tetrahydrofuran / 0.5 h

With 18-crown-6 ether; 4-acetamidobenzenesulfonyl azide; sodium hydride; trifluoroacetic acid; dirhodium tetraacetate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol048157+

Reference yield:

: 158009-86-0
(S_S,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate

: 814256-52-5
(R)-(+)-4-(diethoxyphosphoryloxy)-5-(dimethoxyphosphoryl)-2-phenyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; cyclohexane / 0.25 h / -78 °C

1.2: 84 percent / tetrahydrofuran; cyclohexane / 2 h / -78 °C

2.1: TFA / methanol / 0 - 20 °C

2.2: 90 percent / NEt₃; DMAP / tetrahydrofuran / 3 h / 0 °C

3.1: 83 percent / NaH; 4-acetamidobenzenesulfonyl azide / tetrahydrofuran / 1 h / 20 °C

4.1: 78 percent / rhodium(II) acetate dimer / CH₂Cl₂ / 16 h / 35 °C

5.1: NaH; 18-crown-6 / tetrahydrofuran / 0.08 h / 20 °C

5.2: 81 percent / tetrahydrofuran / 0.5 h

With n-butyllithium; 18-crown-6 ether; 4-acetamidobenzenesulfonyl azide; sodium hydride; trifluoroacetic acid; dirhodium tetraacetate; In tetrahydrofuran; methanol; dichloromethane; cyclohexane;
DOI:10.1021/ol048157+