dibenzyl [1-fluoro-2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate

Base Information

• Chemical Name: dibenzyl [1-fluoro-2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate
• CAS No.: 475628-79-6
• Molecular Formula: C₂₃H₂₈FO₆P
• Molecular Weight: 450.444
• Mol file: 475628-79-6.mol

Synonyms:dibenzyl [1-fluoro-2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate

Chemical Property of dibenzyl [1-fluoro-2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzyl [1-fluoro-2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate

There total 3 articles about dibenzyl [1-fluoro-2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate 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: 55.0%

dibenzyl [2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate (475628-75-2) → dibenzyl [1-fluoro-2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate (475628-79-6) + dibenzyl [1,1-difluoro-2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate (475628-78-5)

Guidance literature:

With 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1002/1099-0690(200208)2002:15<2640::AID-EJOC2640>3.0.CO;2-9

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → dibenzyl [1-fluoro-2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate (475628-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 82 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 20 °C

2.1: nBuLi / tetrahydrofuran / 0.5 h / -78 °C

2.2: 57 percent / tetrahydrofuran / 1 h / -78 °C

3.1: 5 percent / NaH; F-TEDA / tetrahydrofuran; dimethylformamide / 2 h / 20 °C

With n-butyllithium; 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200208)2002:15<2640::AID-EJOC2640>3.0.CO;2-9

Reference yield:

3-(tetrahydropyran-2-yloxy)-propionic acid methyl ester (91267-19-5) → dibenzyl [1-fluoro-2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate (475628-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: nBuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: 57 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 5 percent / NaH; F-TEDA / tetrahydrofuran; dimethylformamide / 2 h / 20 °C

With n-butyllithium; 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200208)2002:15<2640::AID-EJOC2640>3.0.CO;2-9

upstream raw materials:

dibenzyl [2-oxo-4-(tetrahydro-2H-pyranyloxy)butyl]phosphonate

3,4-dihydro-2H-pyran

3-(tetrahydropyran-2-yloxy)-propionic acid methyl ester