diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate

Base Information

• Chemical Name: diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate
• CAS No.: 651718-80-8
• Molecular Formula: C₂₆H₄₇F₂O₅PSi
• Molecular Weight: 536.712
• Mol file: 651718-80-8.mol

Synonyms:diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate

Chemical Property of diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate

There total 5 articles about diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate 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: 75.0%

O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate (651718-79-5) → diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate (651718-80-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1016/j.tet.2003.10.064

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate (651718-80-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2: 35 percent / tetrahydrofuran / 15 h / 65 °C

3: 91 percent / n-Bu₃SnH; AIBN / toluene / 5 h / 100 °C

4: 75 percent / m-CPBA / CH₂Cl₂ / 0.25 h / 20 °C

With 2,6-dimethylpyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2003.10.064

Reference yield:

(2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester (651718-75-1) → diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate (651718-80-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / LiBH₄; B(OMe)3 / tetrahydrofuran / 8 h / 20 °C

2: 81 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3: 35 percent / tetrahydrofuran / 15 h / 65 °C

4: 91 percent / n-Bu₃SnH; AIBN / toluene / 5 h / 100 °C

5: 75 percent / m-CPBA / CH₂Cl₂ / 0.25 h / 20 °C

With 2,6-dimethylpyridine; lithium borohydride; Trimethyl borate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2003.10.064

upstream raw materials:

O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate

triisopropylsilyl trifluoromethanesulfonate

(2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester

5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-D-erythro-pentitol

Downstream raw materials:

diethyl (2S)-4-(benzyloxy)-1,1-difluoro-2-(2-hydroxyethyl)butylphosphonate

diethyl (2R)-4-(benzyloxy)-2-{2-[(diethoxyphosphoryl)oxy]ethyl}-1,1-difluorobutylphosphonate