Fmoc-L-4-Phosphonomethylphenylalanine

Base Information

• Chemical Name: Fmoc-L-4-Phosphonomethylphenylalanine
• CAS No.: 229180-64-7
• Molecular Formula: C25H24NO7P
• Molecular Weight: 481.442
• DSSTox Substance ID: DTXSID30375798
• Nikkaji Number: J1.420.571C
• Wikidata: Q82164474
• Mol file: 229180-64-7.mol

Synonyms:229180-64-7;Fmoc-L-4-Phosphonomethylphenylalanine;Fmoc-4-(phosphonomethyl)-Phe-OH;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(phosphonomethyl)phenyl)propanoic acid;Fmoc-4-(phosphonomethyl)-phenylalanine;Fmoc-L-4-Pmp;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-(phosphonomethyl)phenyl]propanoic acid;SCHEMBL12686916;DTXSID30375798;Fmoc-Phe(4-CH2-PO3H2)-OH;Fmoc-4-phosphomethyl-L-phenylalanine;MFCD00235901;AKOS015837294;AKOS015907801;CS-0179072;E70514;A878386;J-014900;Fmoc-4-(phosphonomethyl)-Phe-OH, >=98.0% (TLC);N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-(phosphonomethyl)-L-phenylalanine;N-(9H-Fluorene-9-ylmethoxycarbonyl)-4-(dihydroxyphosphinylmethyl)-L-phenylalanine;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(phosphonomethyl)phenyl)propanoic acid

Chemical Property of Fmoc-L-4-Phosphonomethylphenylalanine

Chemical Property:

• Refractive Index: 1.647
• PSA: 142.97000
• Density: 1.42 g/cm³
• LogP: 4.28960
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 481.12903910
• Heavy Atom Count: 34
• Complexity: 740

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-4-phosphomethyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=C(C=C4)CP(=O)(O)O)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC=C(C=C4)CP(=O)(O)O)C(=O)O

Technology Process of Fmoc-L-4-Phosphonomethylphenylalanine

There total 4 articles about Fmoc-L-4-Phosphonomethylphenylalanine 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: 98.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + Phosphonomethyltyrosine (142434-81-9) → Fmoc-(4-phosphonomethylphenyl)alanine (229180-64-7)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; Ambient temperature;

DOI:10.1080/00397919908086231

Reference yield:

ethyl N-acetyl-(L)-phenylalaninate (2361-96-8) → Fmoc-(4-phosphonomethylphenyl)alanine (229180-64-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / ZnCl₂ / 8 h / 6 - 8 °C

2: 82 percent / 5 h / Heating

3: 93 percent / HCl / H₂O / 16 h / Heating

4: 98 percent / NaHCO₃ / acetone; H₂O / Ambient temperature

With hydrogenchloride; sodium hydrogencarbonate; zinc(II) chloride; In water; acetone;

DOI:10.1080/00397919908086231

Reference yield:

L-N-acetyl-3-(4-(chloromethyl)phenyl)alanine ethyl ester (130887-73-9) → Fmoc-(4-phosphonomethylphenyl)alanine (229180-64-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / 5 h / Heating

2: 93 percent / HCl / H₂O / 16 h / Heating

3: 98 percent / NaHCO₃ / acetone; H₂O / Ambient temperature

With hydrogenchloride; sodium hydrogencarbonate; In water; acetone;

DOI:10.1080/00397919908086231

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Phosphonomethyltyrosine

ethyl N-acetyl-(L)-phenylalaninate

L-N-acetyl-3-(4-(chloromethyl)phenyl)alanine ethyl ester

Downstream raw materials:

N-acetyl-Glu-Phe-L-(4-phosphonomethylphenyl)alanine-Met-Asp-amide

Refernces