(R)-2-((R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionylamino)-5-(4-methoxy-phenyl)-pentanoic acid

Base Information

• Chemical Name: (R)-2-((R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionylamino)-5-(4-methoxy-phenyl)-pentanoic acid
• CAS No.: 109880-46-8
• Molecular Formula: C₂₈H₃₇N₃O₈
• Molecular Weight: 543.617

Synonyms:(R)-2-((R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionylamino)-5-(4-methoxy-phenyl)-pentanoic acid

Chemical Property of (R)-2-((R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionylamino)-5-(4-methoxy-phenyl)-pentanoic acid

Chemical Property:

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Technology Process of (R)-2-((R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionylamino)-5-(4-methoxy-phenyl)-pentanoic acid

There total 1 articles about (R)-2-((R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionylamino)-5-(4-methoxy-phenyl)-pentanoic acid 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: 73.0%

Boc-D-A2pr(Z)-ONSu (78700-06-8) + (R)-2-amino-5-(4-methoxyphenyl)pentanoic acid → (R)-2-((R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionylamino)-5-(4-methoxy-phenyl)-pentanoic acid (109880-46-8)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1246/bcsj.59.2651

Reference yield: 83.0%

(R)-2-Amino-3-methyl-butyric acid (R)-1-(2-oxo-2-phenyl-ethoxycarbonyl)-ethyl ester; hydrochloride + (R)-2-((R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionylamino)-5-(4-methoxy-phenyl)-pentanoic acid (109880-46-8) → (R)-2-[(R)-2-((R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionylamino)-5-(4-methoxy-phenyl)-pentanoylamino]-3-methyl-butyric acid (R)-1-(2-oxo-2-phenyl-ethoxycarbonyl)-ethyl ester

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1246/bcsj.59.2651

Reference yield:

(R)-2-((R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionylamino)-5-(4-methoxy-phenyl)-pentanoic acid (109880-46-8) → (3R,6R,9R,12R)-9-Aminomethyl-3-isopropyl-6-[3-(4-methoxy-phenyl)-propyl]-12-methyl-1-oxa-4,7,10-triaza-cyclododecane-2,5,8,11-tetraone; hydrobromide

Guidance literature:

Multi-step reaction with 6 steps

1: 83 percent / HOBt, NEt₃, EDC_.HCl / dimethylformamide / 0 °C

2: 91 percent / 90percent AcOH, Zn powder / 8 h / Ambient temperature

3: 98 percent / EDC_.HCl / dimethylformamide / 0 °C

4: 0.5 h / 0 °C

5: 37 percent / dimethylformamide; pyridine / 72 h / Ambient temperature

6: 25percent HBr / acetic acid / 2 h / Ambient temperature

With hydrogen bromide; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; zinc; In pyridine; acetic acid; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.59.2651

upstream raw materials:

Boc-D-A₂pr(Z)-ONSu

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