(S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester
• CAS No.: 192328-70-4
• Molecular Formula: C₁₉H₂₃FN₄O₈
• Molecular Weight: 454.412

Synonyms:(S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester

Chemical Property of (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester

Chemical Property:

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Technology Process of (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester

There total 7 articles about (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid 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: 83.0%

3-cyano-L-alanine methyl ester (192328-68-0) + (2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionic acid (174146-55-5) → (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester (192328-70-4)

Guidance literature:

With acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo970560p

Reference yield: 58.0%

3-cyano-L-alanine methyl ester (192328-68-0) + (2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionic acid pentafluorophenyl ester (192328-69-1) → (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester (192328-70-4)

Guidance literature:

In tetrahydrofuran;

DOI:10.1021/jo970560p

Reference yield:

methyl-β-cyano-L-α-carbo benzoxyaminopropionate (4909-53-9) → (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester (192328-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / H₂ / 10percent Pd-C / methanol / 5 h / 25 °C

2: 83 percent / EDCI, HOAc / tetrahydrofuran / 0 °C

With hydrogen; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/jo970560p

upstream raw materials:

3-cyano-L-alanine methyl ester

(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionic acid

(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionic acid pentafluorophenyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

(R)-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-{(S)-2-[(2R,3R)-2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-3-cyano-propionylamino}-acetic acid tert-butyl ester

(R)-{(S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-3-cyano-propionylamino}-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester

(R)-{(S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionylamino}-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester

C₅₉H₇₃BrClFN₈O₁₇Si

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