Diethyl (((1-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate

Base Information

• Chemical Name: Diethyl (((1-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate
• CAS No.: 132336-36-8
• Molecular Formula: C19H26N3O7P
• Molecular Weight: 439.405
• DSSTox Substance ID: DTXSID10563919
• Mol file: 132336-36-8.mol

Synonyms:132336-36-8;Diethyl (((1-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate;N-[1-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropyl]-2-oxopyrimidin-4-yl]benzamide;Diethyl ({[1-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonate;DTXSID10563919;BCP24064;AKOS016006433;N-Benzoyl rac-Cidofovir Diethyl Phosphonate

Chemical Property of Diethyl (((1-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate

Chemical Property:

• PKA: 8.86±0.20(Predicted)
• Density: 1.33
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 439.15083717
• Heavy Atom Count: 30
• Complexity: 682

Purity/Quality:

97% ^*data from raw suppliers

Diethyl (((1-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(COC(CN1C=CC(=NC1=O)NC(=O)C2=CC=CC=C2)CO)OCC

Technology Process of Diethyl (((1-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate

There total 8 articles about Diethyl (((1-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl)oxy)methyl)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: 92.0%

[(S)-1-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-ylmethyl)-2-trityloxy-ethoxymethyl]-phosphonic acid diethyl ester (132336-35-7) → diethyl (S)-4-N-benzoyl-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine (132336-36-8)

Guidance literature:

With hydrogen bromide; In dichloromethane; at 20 ℃;

Reference yield:

4-N-benzoylcytosine (26661-13-2) → diethyl (S)-4-N-benzoyl-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine (132336-36-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOH / dimethylformamide / 5 h / 105 °C

2: NaH / dimethylformamide / 6 h / 0 °C

3: HCl(g) / CH₂Cl₂ / 0.17 h / 0 - 5 °C

With hydrogenchloride; sodium hydroxide; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)76875-4

Reference yield:

(S)-N1-[2-hydroxy-3-(triphenylmethoxy)propyl]-N4-benzoylcytosine (132336-34-6) → diethyl (S)-4-N-benzoyl-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine (132336-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide / 6 h / 0 °C

2: HCl(g) / CH₂Cl₂ / 0.17 h / 0 - 5 °C

With hydrogenchloride; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)76875-4

upstream raw materials:

[(S)-1-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-ylmethyl)-2-trityloxy-ethoxymethyl]-phosphonic acid diethyl ester

4-N-benzoylcytosine

(S)-N₁-[2-hydroxy-3-(triphenylmethoxy)propyl]-N₄-benzoylcytosine

diethyl (p-toluenesulfonyloxymethane)phosphonate

Downstream raw materials:

N⁴-benzoyl-1-(S)-(3-hydroxy-2-phosphonomethoxypropyl)cytosine

cidofovir