(R)-((R)-2-Benzyloxycarbonylamino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester

Base Information

• Chemical Name: (R)-((R)-2-Benzyloxycarbonylamino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester
• CAS No.: 219911-36-1
• Molecular Formula: C₂₅H₂₉N₃O₈
• Molecular Weight: 499.521

Synonyms:(R)-((R)-2-Benzyloxycarbonylamino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester

Chemical Property of (R)-((R)-2-Benzyloxycarbonylamino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester

Chemical Property:

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Technology Process of (R)-((R)-2-Benzyloxycarbonylamino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester

There total 2 articles about (R)-((R)-2-Benzyloxycarbonylamino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl 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: 76.0%

tert-butyl (R)-(3,5-dihydroxy-4-methoxyphenyl)glycine (174146-51-1) + (R)-2-Benzyloxycarbonylamino-3-cyano-propionic acid → (R)-((R)-2-Benzyloxycarbonylamino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester (219911-36-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1021/jo980880o

Reference yield:

(R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid (4474-86-6) → (R)-((R)-2-Benzyloxycarbonylamino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester (219911-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / DCC / pyridine

2: 76 percent / EDCI, HOBt / dimethylformamide

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; In pyridine; N,N-dimethyl-formamide;

DOI:10.1021/jo980880o

Reference yield: 95.0%

(R)-((R)-2-Benzyloxycarbonylamino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester (219911-36-1) → (R)-((R)-2-Amino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester (219911-38-3)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1021/jo980880o

upstream raw materials:

tert-butyl (R)-(3,5-dihydroxy-4-methoxyphenyl)glycine

(R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid

Downstream raw materials:

(R)-((R)-2-Amino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester

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