(R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester

Base Information

• Chemical Name: (R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester
• CAS No.: 331731-25-0
• Molecular Formula: C₁₆H₂₃FN₂O₆Si
• Molecular Weight: 386.452
• Mol file: 331731-25-0.mol

Synonyms:(R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester

Chemical Property of (R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester

There total 3 articles about (R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine 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: 95.0%

1-[2-(trimethylsilyl)-ethoxycarbonyl-oxy]benzotriazole (113306-55-1) + D-(4-fluoro-3-nitrophenyl)glycine methyl ester (169825-21-2) → (R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester (331731-25-0)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 25 ℃; for 19h;

DOI:10.1021/ja003835i

Reference yield:

4-(bromomethyl)-1-fluoro-2-nitrobenzene (15017-52-4) → (R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester (331731-25-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / n-BuLi; CuCN

2: 87 percent / TFA

3: 95 percent / Et₃N / H₂O; dioxane / 19 h / 25 °C

With n-butyllithium; triethylamine; trifluoroacetic acid; In 1,4-dioxane; water; 1: Schollkopf alkylation;

DOI:10.1021/ja003835i

Reference yield:

(3R,6S)-2,5-dimethoxy-6-isopropyl-3-(4-fluoro-3-nitrophenyl)-3,6-dihydro-1,4-pyrazine (169825-20-1) → (R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester (331731-25-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / TFA

2: 95 percent / Et₃N / H₂O; dioxane / 19 h / 25 °C

With triethylamine; trifluoroacetic acid; In 1,4-dioxane; water;

DOI:10.1021/ja003835i

upstream raw materials:

1-[2-(trimethylsilyl)-ethoxycarbonyl-oxy]benzotriazole

D-(4-fluoro-3-nitrophenyl)glycine methyl ester

4-(bromomethyl)-1-fluoro-2-nitrobenzene

(3R,6S)-2,5-dimethoxy-6-isopropyl-3-(4-fluoro-3-nitrophenyl)-3,6-dihydro-1,4-pyrazine

Downstream raw materials:

C₅₄H₆₆FN₅O₁₆Si

(R)-tert-Butoxycarbonylamino-(3-{3-[(S)-1-[(R)-3-(4-fluoro-3-nitro-phenyl)-2-(2-trimethylsilanyl-ethoxycarbonylamino)-propionylamino]-2-(2-methoxy-ethoxymethoxy)-ethyl]-5-methoxy-phenoxy}-4-methoxy-phenyl)-acetic acid

[(R)-1-[(S)-1-{3-[5-((R)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-2-methoxy-phenoxy]-5-methoxy-phenyl}-2-(2-methoxy-ethoxymethoxy)-ethylcarbamoyl]-2-(4-fluoro-3-nitro-phenyl)-ethyl]-carbamic acid 2-trimethylsilanyl-ethyl ester

Refernces

• 1、 Boger, Dale L.,Kim, Seong Heon,Miyazaki, Susumu,Strittmatter, Harald,Weng, Jian-Hui,Mori, Yoshiki,Rogel, Olivier,Castle, Steven L.,McAtee, J. Jeffrey. "Total synthesis of the teicoplanin aglycon [16]". . p. 7416 - 7417. Retrieved 2007/10/03.