ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate

Base Information

• Chemical Name: ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate
• CAS No.: 685869-24-3
• Molecular Formula: C₁₁H₁₃FN₂O₅
• Molecular Weight: 272.233
• Mol file: 685869-24-3.mol

Synonyms:ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate

Chemical Property of ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate

There total 1 articles about ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate 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:

3-(4-Fluoro-3-nitro-phenyl)-3-hydroxy-2-[(1R,2R,5R)-2-hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-propionic acid ethyl ester → ethyl (2S,3S)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate + ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate (685869-24-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 25 ℃; for 48h; Title compound not separated from byproducts;

DOI:10.1021/ja039795a

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) + ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate (685869-24-3) → ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate (685869-25-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 6h;

DOI:10.1021/ja039795a

Reference yield:

ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate (685869-24-3) → C49H75FN4O15Si2 (685869-35-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

2: Et₃N / dioxane / 18 h / 25 °C

3: aq. LiOH / 2-methyl-propan-2-ol / 18 h / 25 °C

4: 79 percent / NaHCO₃; HATU / tetrahydrofuran / 48 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium hydrogencarbonate; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja039795a

Downstream raw materials:

ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate

(2R,3R)-3-[(tert-butyldimethylsilyl)oxy]-2-[N-[2-trimethylsilylethoxycarbonyl]amino]-3-[(4-fluoro-3-nitro)phenyl]propionic acid

ethyl (2R,3R)-3-[(tert-butyldimethylsilyl)oxy]-2-[N-[2-trimethylsilylethoxycarbonyl]amino]-3-[(4-fluoro-3-nitro)phenyl]propionate

[(8S,11R,14R)-11-[(R)-(4-Fluoro-3-nitro-phenyl)-hydroxy-methyl]-5,18-dimethoxy-8-(2-methoxy-ethoxymethoxymethyl)-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaen-14-yl]-carbamic acid tert-butyl ester