tert-butyl (4R,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

Base Information

• Chemical Name: tert-butyl (4R,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate
• CAS No.: 528523-53-7
• Molecular Formula: C₂₂H₃₄F₂NO₆P
• Molecular Weight: 477.486
• Mol file: 528523-53-7.mol

Synonyms:

Chemical Property of tert-butyl (4R,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (4R,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

There total 11 articles about tert-butyl (4R,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-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:

(4S,5S)-4-[(S)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-phenoxythiocarbonyloxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester → tert-butyl (4R,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate (528523-53-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃; for 2h;

DOI:10.1016/S0960-894X(02)00888-0

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (4R,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate (528523-53-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: methanol / 0.5 h

2.1: imidazole / dimethylformamide / 13.5 h / 20 - 60 °C

3.1: triphenyl phosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C

4.1: DIBAL-H / CH₂Cl₂ / 1.5 h / -20 °C

5.1: p-TsOH / benzene / 0.5 h / Heating

6.1: tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 60 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

8.1: LDA / tetrahydrofuran

8.2: tetrahydrofuran / 4 h / -78 - -70 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

9.2: 1 h / -78 °C

10.1: n-Bu₃SnH; AIBN / toluene / 2 h / 90 °C

With 1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 3.1: Mitsunobu inversion;

DOI:10.1016/S0960-894X(02)00888-0

Reference yield:

(1R,2R)-2-amino-1-phenylpropane-1,3-diol (46032-98-8) → tert-butyl (4R,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate (528523-53-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: methanol / 0.5 h

2.1: imidazole / dimethylformamide / 13.5 h / 20 - 60 °C

3.1: triphenyl phosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C

4.1: DIBAL-H / CH₂Cl₂ / 1.5 h / -20 °C

5.1: p-TsOH / benzene / 0.5 h / Heating

6.1: tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 60 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

8.1: LDA / tetrahydrofuran

8.2: tetrahydrofuran / 4 h / -78 - -70 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

9.2: 1 h / -78 °C

10.1: n-Bu₃SnH; AIBN / toluene / 2 h / 90 °C

With 1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 3.1: Mitsunobu inversion;

DOI:10.1016/S0960-894X(02)00888-0

upstream raw materials:

di-tert-butyl dicarbonate

(1R,2R)-2-amino-1-phenylpropane-1,3-diol

((1R,2R)-2-hydroxy-1-hydroxymethyl-2-phenylethyl)carbamic acid tert-butyl ester

tert-butyl (4R,5S)-4-hydroxymethyl-2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-carboxylate

Downstream raw materials:

diethyl (3R,4S)-1,1-difluoro-4-hydroxy-3-([pentadecylcarbonyl]amino)-4-phenylbutylphosphonate