Diethyl [{[(benzyloxy)carbonyl]amino}(phenyl)methyl]phosphonate

Base Information

• Chemical Name: Diethyl [{[(benzyloxy)carbonyl]amino}(phenyl)methyl]phosphonate
• CAS No.: 38428-05-6
• Molecular Formula: C19H24NO5P
• Molecular Weight: 377.377
• DSSTox Substance ID: DTXSID20500113
• Nikkaji Number: J324.001K
• Mol file: 38428-05-6.mol

Synonyms:38428-05-6;DTXSID20500113;Diethyl [{[(benzyloxy)carbonyl]amino}(phenyl)methyl]phosphonate

Chemical Property of Diethyl [{[(benzyloxy)carbonyl]amino}(phenyl)methyl]phosphonate

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 377.13920986
• Heavy Atom Count: 26
• Complexity: 451

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(C1=CC=CC=C1)NC(=O)OCC2=CC=CC=C2)OCC

Technology Process of Diethyl [{[(benzyloxy)carbonyl]amino}(phenyl)methyl]phosphonate

There total 14 articles about Diethyl [{[(benzyloxy)carbonyl]amino}(phenyl)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%

O-benzyl carbamate (621-84-1) + benzaldehyde (100-52-7) + phosphonic acid diethyl ester (762-04-9) → diethyl ether of α-(N-benzyloxycarbonyl)aminobenzylphosphonic acid (38428-05-6)

Guidance literature:

With thionyl chloride; acetic acid; 1) room temperature, 20 min, 2) reflux, 6 h;

DOI:10.1055/s-1990-26927

Reference yield: 91.0%

[phenyl-(toluene-4-sulfonyl)-methyl]-carbamic acid benzyl ester (372199-85-4) + diethyl trimethylsilyl phosphite (13716-45-5) → diethyl ether of α-(N-benzyloxycarbonyl)aminobenzylphosphonic acid (38428-05-6)

Guidance literature:

With iron(III) chloride; In dichloromethane; at 20 ℃; for 2h; Reagent/catalyst; Catalytic behavior; Inert atmosphere;

DOI:10.1080/00397911.2016.1270323

Reference yield: 86.0%

ethanol (64-17-5) + O,O-diphenyl {[(benzyloxy)carbonyl]amino}(phenyl)methylphosphonate (65164-84-3,125882-49-7,125882-56-6) → diethyl ether of α-(N-benzyloxycarbonyl)aminobenzylphosphonic acid (38428-05-6)

Guidance literature:

With potassium fluoride; 18-crown-6 ether; 1.) reflux, 10 min, 2.) room temp., overnight;

DOI:10.1055/s-1982-29817

upstream raw materials:

ethanol

O,O-diphenyl {[(benzyloxy)carbonyl]amino}(phenyl)methylphosphonate

O-benzyl carbamate

benzaldehyde

Downstream raw materials:

diethyl 1-aminophenylmethylphosphonate

ethyl hydrogen α-(benzyloxycarbonylamino)benzylphosphonate

Diethyl-α-Aminobenzylphosphonato-hydrobromid

2-Benzyloxy-carbonylglycylamino-benzylphosphonsaeure-diaethylester