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

Base Information

• Chemical Name: diethyl (3R,4S)-1,1-difluoro-4-hydroxy-3-([pentadecylcarbonyl]amino)-4-phenylbutylphosphonate
• CAS No.: 528523-57-1
• Molecular Formula: C₃₀H₅₂F₂NO₅P
• Molecular Weight: 575.717
• Mol file: 528523-57-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about diethyl (3R,4S)-1,1-difluoro-4-hydroxy-3-([pentadecylcarbonyl]amino)-4-phenylbutylphosphonate 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: 69.0%

diethyl (3R,4S)-3-[(tert-butoxycarbonyl)amino]-1,1-difluoro-4-hydroxy-4-phenylbutylphosphonate (1178980-70-5) + n-hexadecanoyl chloride (112-67-4) → diethyl (3R,4S)-1,1-difluoro-4-hydroxy-3-([pentadecylcarbonyl]amino)-4-phenylbutylphosphonate (528523-57-1)

Guidance literature:

diethyl (3R,4S)-3-[(tert-butoxycarbonyl)amino]-1,1-difluoro-4-hydroxy-4-phenylbutylphosphonate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

n-hexadecanoyl chloride; With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo9008782

Reference yield:

((3R,4S)-3-Amino-1,1-difluoro-4-hydroxy-4-phenyl-butyl)-phosphonic acid diethyl ester + n-hexadecanoyl chloride (112-67-4) → diethyl (3R,4S)-1,1-difluoro-4-hydroxy-3-([pentadecylcarbonyl]amino)-4-phenylbutylphosphonate (528523-57-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;

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

Reference yield:

(1R,2R)-2-amino-1-phenylpropane-1,3-diol (46032-98-8) → diethyl (3R,4S)-1,1-difluoro-4-hydroxy-3-([pentadecylcarbonyl]amino)-4-phenylbutylphosphonate (528523-57-1)

Guidance literature:

Multi-step reaction with 12 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

11.1: 3 M aq. HCl / ethyl acetate / 1 h / 20 °C

12.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; 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; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 3.1: Mitsunobu inversion;

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

upstream raw materials:

n-hexadecanoyl chloride

(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