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

Base Information

• Chemical Name: ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate
• CAS No.: 685869-25-4
• Molecular Formula: C₁₇H₂₇FN₂O₅Si
• Molecular Weight: 386.496

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

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

Chemical Property:

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

There total 2 articles about ethyl (2R,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:

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:

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 (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate (685869-25-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HCl / tetrahydrofuran / 48 h / 25 °C

2: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

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

DOI:10.1021/ja039795a

Reference yield:

1-[2-(trimethylsilyl)-ethoxycarbonyl-oxy]benzotriazole (113306-55-1) + ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate (685869-25-4) → ethyl (2R,3R)-3-[(tert-butyldimethylsilyl)oxy]-2-[N-[2-trimethylsilylethoxycarbonyl]amino]-3-[(4-fluoro-3-nitro)phenyl]propionate (685869-26-5)

Guidance literature:

With triethylamine; In 1,4-dioxane; at 25 ℃; for 18h;

DOI:10.1021/ja039795a

upstream raw materials:

t-butyldimethylsiyl triflate

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

Downstream raw materials:

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

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

[(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

{11-[(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-8-hydroxymethyl-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]eicosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaen-14-yl}-carbamic acid tert-butyl ester

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