{(S)-4-Benzyloxycarbonylamino-4-[(S)-3-cyano-1-methyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propylcarbamoyl]-butyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(S)-4-Benzyloxycarbonylamino-4-[(S)-3-cyano-1-methyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propylcarbamoyl]-butyl}-carbamic acid tert-butyl ester
• CAS No.: 199467-22-6
• Molecular Formula: C₄₁H₄₅N₄O₆P
• Molecular Weight: 720.805

Synonyms:{(S)-4-Benzyloxycarbonylamino-4-[(S)-3-cyano-1-methyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propylcarbamoyl]-butyl}-carbamic acid tert-butyl ester

Chemical Property of {(S)-4-Benzyloxycarbonylamino-4-[(S)-3-cyano-1-methyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propylcarbamoyl]-butyl}-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of {(S)-4-Benzyloxycarbonylamino-4-[(S)-3-cyano-1-methyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propylcarbamoyl]-butyl}-carbamic acid tert-butyl ester

There total 3 articles about {(S)-4-Benzyloxycarbonylamino-4-[(S)-3-cyano-1-methyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propylcarbamoyl]-butyl}-carbamic 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:

Z-Orn(Boc)-OH (7733-29-1,199924-46-4) + 4-amino-2-(triphenyl-λ5-phosphanylidene)-3-oxo-pentanenitrile (199467-21-5) → {(S)-4-Benzyloxycarbonylamino-4-[(S)-3-cyano-1-methyl-2-oxo-3-(triphenyl-λ5-phosphanylidene)-propylcarbamoyl]-butyl}-carbamic acid tert-butyl ester (199467-22-6)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 20h; Yield given; Ambient temperature;

DOI:10.1021/jo9718253

Reference yield:

cyanomethylene triphenylphosphorane (16640-68-9) → {(S)-4-Benzyloxycarbonylamino-4-[(S)-3-cyano-1-methyl-2-oxo-3-(triphenyl-λ5-phosphanylidene)-propylcarbamoyl]-butyl}-carbamic acid tert-butyl ester (199467-22-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 54 percent / DMAP; EDCI / CH₂Cl₂ / 4 h / 20 °C

2: piperidine / 0.25 h / 20 °C

3: 1.4045 g / HOBt; EDCI / CH₂Cl₂ / 20 h / 20 °C

With piperidine; dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1016/S0040-4020(03)00860-3

Reference yield:

[3-cyano-1-methyl-2-oxo-3-(triphenyl-λ5-phosphanylidene)-propyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (199467-20-4) → {(S)-4-Benzyloxycarbonylamino-4-[(S)-3-cyano-1-methyl-2-oxo-3-(triphenyl-λ5-phosphanylidene)-propylcarbamoyl]-butyl}-carbamic acid tert-butyl ester (199467-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: piperidine / 0.25 h / 20 °C

2: 1.4045 g / HOBt; EDCI / CH₂Cl₂ / 20 h / 20 °C

With piperidine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1016/S0040-4020(03)00860-3

upstream raw materials:

Z-Orn(Boc)-OH

4-amino-2-(triphenyl-λ⁵-phosphanylidene)-3-oxo-pentanenitrile

cyanomethylene triphenylphosphorane

[3-cyano-1-methyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Downstream raw materials:

[(S)-4-Benzyloxycarbonylamino-4-((S)-3-cyano-1-methyl-2,3-dioxo-propylcarbamoyl)-butyl]-carbamic acid tert-butyl ester

Eurystatin A

(3-isobutyl-7-methyl-2,5,6,9-tetraoxo-1,4,8-triazacyclotridec-10-yl)-carbamic acid benzyl ester

2-[3-(2-benzyloxycarbonylamino-5-tert-butoxycarnonylaminopentanoylamino)-2-oxo-butyrylamino]-4-methylpentanoic acid tert-butyl ester

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