N-Boc-(4-diethylphosphonomethyl)-L-phenylalanine

Base Information

• Chemical Name: N-Boc-(4-diethylphosphonomethyl)-L-phenylalanine
• CAS No.: 142348-55-8
• Molecular Formula: C19H30NO7P
• Molecular Weight: 415.41800
• DSSTox Substance ID: DTXSID00454089
• Nikkaji Number: J982.417K
• Wikidata: Q82275423
• Mol file: 142348-55-8.mol

Synonyms:142348-55-8;N-Boc-(4-diethylphosphonomethyl)-L-phenylalanine;(s)-2-tert-butoxycarbonylamino-3-[4-(diethoxy-phosphorylmethyl)-phenyl]-propionic acid;(2S)-3-[4-(diethoxyphosphorylmethyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-((diethoxyphosphoryl)methyl)phenyl)propanoic acid;DTXSID00454089;(2S)-2-[(tert-Butoxycarbonyl)amino]-3-[4-[(diethoxyphosphinyl)methyl]phenyl]propionic acid

Chemical Property of N-Boc-(4-diethylphosphonomethyl)-L-phenylalanine

Chemical Property:

• PSA: 124.46000
• LogP: 4.17750
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 415.17598929
• Heavy Atom Count: 28
• Complexity: 543

Purity/Quality:

98.5% ^*data from raw suppliers

N-BOC-(4-DIETHYLPHOSPHONOMETHYL)-L-PHENYLALANINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CC1=CC=C(C=C1)CC(C(=O)O)NC(=O)OC(C)(C)C)OCC
• Isomeric SMILES: CCOP(=O)(CC1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)OCC

Technology Process of N-Boc-(4-diethylphosphonomethyl)-L-phenylalanine

There total 15 articles about N-Boc-(4-diethylphosphonomethyl)-L-phenylalanine 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: 75.0%

diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate (213127-96-9) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propanoic acid (142348-55-8)

Guidance literature:

With jones reagent; In acetone; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(98)00586-9

Reference yield: 40.0%

ethyl (N-tert-butyloxycarbonyl)-(4-diethylphosphonomethyl)-D,L-phenylalaninate (142348-47-8) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propanoic acid (142348-55-8)

Guidance literature:

DOI:10.1016/S0957-4166(00)82297-1

Reference yield:

4-(diethoxyphosphorylmethyl)-1-bromomethyl-phenyl (108228-81-5) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propanoic acid (142348-55-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 76 percent / NaH / tetrahydrofuran / 0.5 h / 20 °C

2: 79 percent / NaBH₄ / methanol / 2 h / 20 °C

3: 97 percent / lipase PS / tetrahydrofuran / 2 h / 25 °C / Enzymatic reaction; 2 equiv. vinyl acetate

4: Jones reagent / acetone / 4 h / 20 °C

5: 52 percent / diphenylphosphoryl azide; triethylamine / benzene / 24 h / Heating

6: 88 percent / H₂ / Pd-C / ethyl acetate / 12 h / 20 °C / 760 Torr

7: 77 percent / aq. MeOH; K₂CO₃ / 1 h

8: 75 percent / Jones reagent / acetone / 1 h / 20 °C

With methanol; sodium tetrahydroborate; jones reagent; Lipase PS; diphenylphosphoranyl azide; hydrogen; sodium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; acetone; benzene; 1: Substitution / 2: Reduction / 3: Acetylation / 4: Oxidation / 5: Rearrangement / 6: Substitution / 7: Hydrolysis / 8: Oxidation;

DOI:10.1016/S0040-4020(98)00586-9

upstream raw materials:

ethyl (N-tert-butyloxycarbonyl)-(4-diethylphosphonomethyl)-D,L-phenylalaninate

diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate

diethyl 4-methylbenzylphosphonate

4-(diethoxyphosphorylmethyl)-1-bromomethyl-phenyl

Downstream raw materials:

Phosphonomethyltyrosine

4-(diethylphosphonomethyl)-L-phenylalanine trifluoroacetate