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

Base Information

• Chemical Name: methyl (2S,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate
• CAS No.: 174146-43-1
• Molecular Formula: C₁₆H₂₅FN₂O₅Si
• Molecular Weight: 372.469
• Mol file: 174146-43-1.mol

Synonyms:methyl (2S,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate

Chemical Property of methyl (2S,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate

There total 3 articles about methyl (2S,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate 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: 85.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2S,3R)-2-Amino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionic acid methyl ester (174146-42-0) → methyl (2S,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate (174146-43-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1021/jo970560p

Reference yield:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → methyl (2S,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate (174146-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.2: (Cp)2ZrCl₂ / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.3: 60 percent / tetrahydrofuran; hexane / 48 h / -78 °C

2.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

3.1: 89 percent / aq. HCl / tetrahydrofuran; acetonitrile / 18 h / 25 °C

With 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;

DOI:10.1021/ja039795a

Reference yield:

(R)-(4-fluoro-3-nitrophenyl)-((2R,5S)-2,5-dihydro-5-isopropyl-3,6-dimethoxypyrazin-2-yl)methanol (188446-44-8) → methyl (2S,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate (174146-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

2: 89 percent / aq. HCl / tetrahydrofuran; acetonitrile / 18 h / 25 °C

With 2,6-dimethylpyridine; hydrogenchloride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja039795a

upstream raw materials:

t-butyldimethylsiyl triflate

(2S,3R)-2-Amino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionic acid methyl ester

4-fluoro-3-nitrobenzaldehyde

(R)-(4-fluoro-3-nitrophenyl)-((2R,5S)-2,5-dihydro-5-isopropyl-3,6-dimethoxypyrazin-2-yl)methanol

Downstream raw materials:

(2S,3R)-2-[(R)-2-(3-Bromo-4-methoxy-phenyl)-2-tert-butoxycarbonylamino-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

C₃₉H₄₉BrN₄O₁₃Si

C₃₉H₄₉BrClN₃O₁₁Si

(2S,3R)-2-{(R)-2-(3-Bromo-4-methoxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dihydroxy-4-methoxy-phenyl)-acetylamino]-acetylamino}-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester