L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]-

Base Information

• Chemical Name: L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]-
• CAS No.: 160751-42-8
• Molecular Formula: C14H20F2NO5P
• Molecular Weight: 351.287
• DSSTox Substance ID: DTXSID10471207
• Nikkaji Number: J1.946.504G
• Wikidata: Q82299660
• Mol file: 160751-42-8.mol

Synonyms:L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]-;160751-42-8;SCHEMBL2423462;DTXSID10471207;SNSFIWGJZZYFDH-LBPRGKRZSA-N;(S)-2-Amino-3-(4-((diethoxyphosphoryl)difluoromethyl)phenyl)propanoic acid

Chemical Property of L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]-

Chemical Property:

• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 351.10471606
• Heavy Atom Count: 23
• Complexity: 431

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(C1=CC=C(C=C1)CC(C(=O)O)N)(F)F)OCC
• Isomeric SMILES: CCOP(=O)(C(C1=CC=C(C=C1)C[C@@H](C(=O)O)N)(F)F)OCC

Technology Process of L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]-

There total 5 articles about L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]- 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: 100.0%

(3S,5S,6R)-3-{4-[(Diethoxy-phosphoryl)-difluoro-methyl]-benzyl}-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (174678-81-0) → 4-<(diethylphosphono)difluoromethyl>-L-phenylalanine (160751-42-8)

Guidance literature:

With hydrogen; palladium dichloride; In tetrahydrofuran; methanol; ethanol; for 20h; under 2585.7 Torr;

DOI:10.1021/jo9517508

Reference yield:

4-bromomethylbenzoic Acid (6232-88-8) → 4-<(diethylphosphono)difluoromethyl>-L-phenylalanine (160751-42-8)

Guidance literature:

Multi-step reaction with 5 steps

1: phosphorus tribromide / 3 h / Heating

2: 1.9 g / toluene / 0.67 h / 0 °C

3: 52 percent / (diethylamido)sulfur trifluoride / Ambient temperature

4: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C

5: 100 percent / H₂ / PdCl₂ / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr

With N,N,N,N,N,N-hexamethylphosphoric triamide; (diethylamido)sulfur trifluoride; hydrogen; phosphorus tribromide; lithium hexamethyldisilazane; palladium dichloride; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1021/jo9517508

Reference yield:

4-(bromomethyl)benzoyl bromide (876-07-3) → 4-<(diethylphosphono)difluoromethyl>-L-phenylalanine (160751-42-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.9 g / toluene / 0.67 h / 0 °C

2: 52 percent / (diethylamido)sulfur trifluoride / Ambient temperature

3: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C

4: 100 percent / H₂ / PdCl₂ / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr

With N,N,N,N,N,N-hexamethylphosphoric triamide; (diethylamido)sulfur trifluoride; hydrogen; lithium hexamethyldisilazane; palladium dichloride; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1021/jo9517508

upstream raw materials:

(3S,5S,6R)-3-{4-[(Diethoxy-phosphoryl)-difluoro-methyl]-benzyl}-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

4-bromomethylbenzoic Acid

4-(bromomethyl)benzoyl bromide

diethyl ((4-(α-bromomethyl)phenyl)oxomethyl)phosphonate

Downstream raw materials:

(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid

(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[difluoro(phosphono)methyl]phenyl}propanoic acid