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

Base Information

• Chemical Name: 5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-D-erythro-pentitol
• CAS No.: 651718-76-2
• Molecular Formula: C₁₇H₂₇F₂O₅PS
• Molecular Weight: 412.435
• Mol file: 651718-76-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-D-erythro-pentitol 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: 95.0%

(2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester (651718-75-1) → 5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-D-erythro-pentitol (651718-76-2)

Guidance literature:

With lithium borohydride; Trimethyl borate; In tetrahydrofuran; at 20 ℃; for 8h;

DOI:10.1016/j.tet.2003.10.064

Reference yield: 81.0%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + 5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-D-erythro-pentitol (651718-76-2) → 5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-1-O-(triisopropylsilyl)-D-erythro-pentitol (651718-77-3)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/j.tet.2003.10.064

Reference yield:

5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-D-erythro-pentitol (651718-76-2) → diethyl (2S)-4-(benzyloxy)-1,1-difluoro-2-(2-hydroxyethyl)butylphosphonate (651718-81-9)

Guidance literature:

Multi-step reaction with 5 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

5: 100 percent / p-TsOH*H₂O / methanol / 15 h / 20 °C

With 2,6-dimethylpyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1016/j.tet.2003.10.064

upstream raw materials:

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

Downstream raw materials:

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

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

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

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