L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]-N-[(9H-fluoren-9-ylmethoxy)carb onyl]-, methyl ester

Base Information

• Chemical Name: L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]-N-[(9H-fluoren-9-ylmethoxy)carb onyl]-, methyl ester
• CAS No.: 156017-44-6
• Molecular Formula: C30H32F2NO7P
• Molecular Weight: 587.557
• Mol file: 156017-44-6.mol

Synonyms:

Chemical Property of L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]-N-[(9H-fluoren-9-ylmethoxy)carb onyl]-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]-N-[(9H-fluoren-9-ylmethoxy)carb onyl]-, methyl ester

There total 10 articles about L-Phenylalanine, 4-[(diethoxyphosphinyl)difluoromethyl]-N-[(9H-fluoren-9-ylmethoxy)carb onyl]-, methyl ester 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: 80.0%

diethyl (bromodifluoromethyl)phosphonate (65094-22-6) + (S)-methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-iodophenyl)propanoate (195258-67-4) → Fmoc-(4-diethyl phosphonodifluoromethyl)-Phe-OMe (156017-44-6)

Guidance literature:

diethyl (bromodifluoromethyl)phosphonate; With chloro-trimethyl-silane; cadmium; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

(S)-methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-iodophenyl)propanoate; With copper(l) chloride; In N,N-dimethyl-formamide; for 48h;

Reference yield:

N-fmoc-4-iodo-(L)-phenylalanine (82565-68-2,205526-29-0) → Fmoc-(4-diethyl phosphonodifluoromethyl)-Phe-OMe (156017-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SOCl₂ / 0 - 20 °C

2.1: Cd; TMSCl / dimethylformamide

2.2: 4.92 g / CuCl / dimethylformamide / 96 h / 20 °C

With chloro-trimethyl-silane; thionyl chloride; cadmium; In N,N-dimethyl-formamide;

DOI:10.1021/jm061146x

Reference yield:

N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester (82911-78-2) → Fmoc-(4-diethyl phosphonodifluoromethyl)-Phe-OMe (156017-44-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / -5 °C

2: NaI / acetone / Ambient temperature

3: 1.) zinc dust / 2.) (Ph₃P)2PdCl₂ / 1.) THF/N,N-dimethylacetamide, 65 deg C, 1 h, 2.) THF/N,N-dimethylacetamide, 65 deg C, 5 h

With pyridine; sodium iodide; zinc; bis-triphenylphosphine-palladium(II) chloride; In acetone;

DOI:10.1016/S0040-4039(00)75835-7

upstream raw materials:

[Difluoro-(4-iodo-phenyl)-methyl]-phosphonic acid diethyl ester

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodo-propionic acid methyl ester

diethyl (bromodifluoromethyl)phosphonate

(S)-methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-iodophenyl)propanoate

Downstream raw materials:

C₄₇H₅₉Cl₂F₄N₇O₁₅P₂

C₃₅H₃₅ClF₂N₃O₉P

C₃₅H₃₆ClF₂N₄O₈P

C₃₆H₃₇ClF₂N₃O₉P