3-{4-[ethoxy-(hydroxy-phenyl-methyl)-phosphinoylmethyl]-phenyl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester

Base Information

• Chemical Name: 3-{4-[ethoxy-(hydroxy-phenyl-methyl)-phosphinoylmethyl]-phenyl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester
• CAS No.: 313342-62-0
• Molecular Formula: C₄₁H₄₀NO₇P
• Molecular Weight: 689.745

Synonyms:3-{4-[ethoxy-(hydroxy-phenyl-methyl)-phosphinoylmethyl]-phenyl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester

Chemical Property of 3-{4-[ethoxy-(hydroxy-phenyl-methyl)-phosphinoylmethyl]-phenyl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester

Chemical Property:

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Technology Process of 3-{4-[ethoxy-(hydroxy-phenyl-methyl)-phosphinoylmethyl]-phenyl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester

There total 8 articles about 3-{4-[ethoxy-(hydroxy-phenyl-methyl)-phosphinoylmethyl]-phenyl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl 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:

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) → 3-{4-[ethoxy-(hydroxy-phenyl-methyl)-phosphinoylmethyl]-phenyl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester (313342-62-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 64 percent / PPh₃; imidazole; iodine / acetonitrile; diethyl ether / 0.75 h / 0 °C

2.1: Zn; TMSCl / various solvent(s)

2.2: 77 percent / (2-furyl)3P; Pd₂dba3 / N,N-dimethyl-acetamide; tetrahydrofuran / 60 °C

3.1: 73 percent / TMSCl / CH₂Cl₂; ethanol / 20 °C

4.1: 78 percent / iPr₂EtN / CH₂Cl₂ / 4.5 h / 20 °C

5.1: HBr; AcOH

6.1: pyridine; DMAP

With pyridine; 1H-imidazole; dmap; chloro-trimethyl-silane; hydrogen bromide; iodine; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; In diethyl ether; ethanol; dichloromethane; acetonitrile; 1.1: Iodination / 2.1: Metallation / 2.2: Arylation / 3.1: dealkylation / 4.1: Addition / 5.1: acidolysis / 6.1: Acylation;

DOI:10.1016/S0960-894X(00)00476-5

Reference yield:

1-bromomethyl-4-iodobenzene (16004-15-2) → 3-{4-[ethoxy-(hydroxy-phenyl-methyl)-phosphinoylmethyl]-phenyl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester (313342-62-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 94 percent / NaH / tetrahydrofuran / -10 - 20 °C

2.1: Zn; TMSCl / various solvent(s)

2.2: 77 percent / (2-furyl)3P; Pd₂dba3 / N,N-dimethyl-acetamide; tetrahydrofuran / 60 °C

3.1: 73 percent / TMSCl / CH₂Cl₂; ethanol / 20 °C

4.1: 78 percent / iPr₂EtN / CH₂Cl₂ / 4.5 h / 20 °C

5.1: HBr; AcOH

6.1: pyridine; DMAP

With pyridine; dmap; chloro-trimethyl-silane; hydrogen bromide; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Alkylation / 2.1: Metallation / 2.2: Arylation / 3.1: dealkylation / 4.1: Addition / 5.1: acidolysis / 6.1: Acylation;

DOI:10.1016/S0960-894X(00)00476-5

Reference yield:

(R)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-iodopropanoate (65926-39-8) → 3-{4-[ethoxy-(hydroxy-phenyl-methyl)-phosphinoylmethyl]-phenyl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester (313342-62-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Zn; TMSCl / various solvent(s)

1.2: 77 percent / (2-furyl)3P; Pd₂dba3 / N,N-dimethyl-acetamide; tetrahydrofuran / 60 °C

2.1: 73 percent / TMSCl / CH₂Cl₂; ethanol / 20 °C

3.1: 78 percent / iPr₂EtN / CH₂Cl₂ / 4.5 h / 20 °C

4.1: HBr; AcOH

5.1: pyridine; DMAP

With pyridine; dmap; chloro-trimethyl-silane; hydrogen bromide; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In ethanol; dichloromethane; 1.1: Metallation / 1.2: Arylation / 2.1: dealkylation / 3.1: Addition / 4.1: acidolysis / 5.1: Acylation;

DOI:10.1016/S0960-894X(00)00476-5

upstream raw materials:

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

N-benzyloxycarbonyl-L-serine benzyl ester

1-bromomethyl-4-iodobenzene

(R)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-iodopropanoate

Downstream raw materials:

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-{4-[hydroxy-(hydroxy-phenyl-methyl)-phosphinoylmethyl]-phenyl}-propionic acid

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