N^α-Boc-4-(diethoxyphosphinyl)-L-phenylalanine methyl ester

Base Information

• Chemical Name: N^α-Boc-4-(diethoxyphosphinyl)-L-phenylalanine methyl ester
• CAS No.: 154483-79-1
• Molecular Formula: C₁₉H₃₀NO₇P
• Molecular Weight: 415.423
• Mol file: 154483-79-1.mol

Synonyms:N^α-Boc-4-(diethoxyphosphinyl)-L-phenylalanine methyl ester

Chemical Property of N^α-Boc-4-(diethoxyphosphinyl)-L-phenylalanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of N^α-Boc-4-(diethoxyphosphinyl)-L-phenylalanine methyl ester

There total 4 articles about N^α-Boc-4-(diethoxyphosphinyl)-L-phenylalanine 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: 86.0%

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate (112766-18-4) + phosphonic acid diethyl ester (762-04-9) → Nα-Boc-4-(diethoxyphosphinyl)-L-phenylalanine methyl ester (154483-79-1)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate; palladium diacetate; triethylamine; In tetrahydrofuran; at 68 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/adsc.200900590

Reference yield: 80.0%

Diethyl phosphonate (762-04-9,123-22-8) + methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate (112766-18-4) → Nα-Boc-4-(diethoxyphosphinyl)-L-phenylalanine methyl ester (154483-79-1)

Guidance literature:

With 2-methylmorpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 70 ℃; for 15h;

DOI:10.1021/jm00031a012

Reference yield: 40.0%

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate (112766-18-4) + triethyl phosphite (122-52-1) → Nα-Boc-4-(diethoxyphosphinyl)-L-phenylalanine methyl ester (154483-79-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In acetonitrile; at 25 ℃; for 24h; Inert atmosphere; UV-irradiation; Green chemistry;

DOI:10.1039/d1cc03496k

upstream raw materials:

Diethyl phosphonate

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

phosphonic acid diethyl ester

Downstream raw materials:

(S)-2-Amino-3-[4-(diethoxy-phosphoryl)-phenyl]-propionic acid

N^α-Boc-4-(diethoxyphosphinyl)-L-phenylalanine

Refernces

• 1、 Kalek, Marcin,Jezowska, Martina,Stawinski, Jacek. "Preparation of arylphosphonates by palladium(O)-catalyzed cross-coupling in the presence of acetate additives: Synthetic and mechanistic studies". experimental part. p. 3207 - 3216. Retrieved 2010/04/26.