methyl (2R,3S)-3-tert-butoxy-carbonylamino-2-hydroxy-3-(4-fluorophenyl)propionate

Base Information

• Chemical Name: methyl (2R,3S)-3-tert-butoxy-carbonylamino-2-hydroxy-3-(4-fluorophenyl)propionate
• CAS No.: 154306-85-1
• Molecular Formula: C₁₅H₂₀FNO₅
• Molecular Weight: 313.326

Synonyms:methyl (2R,3S)-3-tert-butoxy-carbonylamino-2-hydroxy-3-(4-fluorophenyl)propionate

Chemical Property of methyl (2R,3S)-3-tert-butoxy-carbonylamino-2-hydroxy-3-(4-fluorophenyl)propionate

Chemical Property:

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Technology Process of methyl (2R,3S)-3-tert-butoxy-carbonylamino-2-hydroxy-3-(4-fluorophenyl)propionate

There total 16 articles about methyl (2R,3S)-3-tert-butoxy-carbonylamino-2-hydroxy-3-(4-fluorophenyl)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: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S)-3-Azido-3-(4-fluoro-phenyl)-2-hydroxy-propionic acid methyl ester (186758-11-2) → methyl (2R,3S)-3-tert-butoxy-carbonylamino-2-hydroxy-3-(4-fluorophenyl)propionate (154306-85-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3.5h; under 760 Torr; Ambient temperature;

DOI:10.3987/com-96-s20

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + methyl (2R,3S)-3-amino-2-hydroxy-3-(4-fluoro-phenyl)propionate (157240-38-5) → methyl (2R,3S)-3-tert-butoxy-carbonylamino-2-hydroxy-3-(4-fluorophenyl)propionate (154306-85-1)

Guidance literature:

With sodium carbonate; In dichloromethane; at 20 ℃; for 72h; Yield given;

DOI:10.1016/S0040-4039(00)61724-0

Reference yield:

methyl (2R,3S)-2-hydroxy-3-[(S)-1-phenyl]ethylamino-3-(4-fluorophenyl)propionate (154306-84-0) → methyl (2R,3S)-3-tert-butoxy-carbonylamino-2-hydroxy-3-(4-fluorophenyl)propionate (154306-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / palladium/C 3percent / methanol; acetic acid / 4 h / 65 °C / 17841.6 Torr

2: Na₂CO₃ / CH₂Cl₂ / 72 h / 20 °C

With hydrogen; sodium carbonate; palladium on activated charcoal; In methanol; dichloromethane; acetic acid;

DOI:10.1016/S0040-4039(00)61724-0

upstream raw materials:

di-tert-butyl dicarbonate

methyl (2R,3S)-3-amino-2-hydroxy-3-(4-fluoro-phenyl)propionate

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

methyl (2E)-3-(4-fluorophenyl)-2-propenoate

Downstream raw materials:

(4S,5R)-4-(4-Fluoro-phenyl)-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester

(4S,5R)-4-(4-Fluoro-phenyl)-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester

3'-dephenyl-3'-(4-fluorophenyl)docetaxel

C₄₉H₅₄Cl₆FNO₁₈

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