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

Base Information

• Chemical Name: O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate
• CAS No.: 651718-79-5
• Molecular Formula: C₂₆H₄₇F₂O₄PSSi
• Molecular Weight: 552.779
• Mol file: 651718-79-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate 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: 91.0%

5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol (651718-91-1) → O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate (651718-79-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 100 ℃; for 5h;

DOI:10.1016/j.tet.2003.10.064

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate (651718-79-5)

Guidance literature:

Multi-step reaction with 3 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

With 2,6-dimethylpyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 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) → O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate (651718-79-5)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1016/j.tet.2003.10.064

upstream raw materials:

5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol

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

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

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