{1-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-cyclopropyl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {1-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-cyclopropyl}-carbamic acid benzyl ester
• CAS No.: 558475-58-4
• Molecular Formula: C₃₂H₂₇N₂O₃P
• Molecular Weight: 518.552
• Mol file: 558475-58-4.mol

Synonyms:{1-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-cyclopropyl}-carbamic acid benzyl ester

Chemical Property of {1-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-cyclopropyl}-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {1-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-cyclopropyl}-carbamic acid benzyl ester

There total 1 articles about {1-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-cyclopropyl}-carbamic acid benzyl 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: 63.0%

(benzyloxycarbonylamino)cyclopropanecarboxylic acid (84677-06-5) + cyanomethylene triphenylphosphorane (16640-68-9) → {1-[2-Cyano-2-(triphenyl-λ5-phosphanylidene)-acetyl]-cyclopropyl}-carbamic acid benzyl ester (558475-58-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 8h;

DOI:10.1016/S0960-894X(03)00031-3

Reference yield: 84.0%

glycine tert-butyl ester hydrochloride (27532-96-3) + {1-[2-Cyano-2-(triphenyl-λ5-phosphanylidene)-acetyl]-cyclopropyl}-carbamic acid benzyl ester (558475-58-4) → [2-(1-benzyloxycarbonylamino-cyclopropyl)-2-oxo-acetylamino]-acetic acid tert-butyl ester (558475-60-8)

Guidance literature:

{1-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-cyclopropyl}-carbamic acid benzyl ester; With ozone; In dichloromethane; at -78 ℃;

glycine tert-butyl ester hydrochloride; In dichloromethane; for 1h;

DOI:10.1016/S0960-894X(03)00031-3

Reference yield:

{1-[2-Cyano-2-(triphenyl-λ5-phosphanylidene)-acetyl]-cyclopropyl}-carbamic acid benzyl ester (558475-58-4) → (2-{1-[(S)-3-Cyclohexyl-2-((2S,3S)-3-methyl-2-{(S)-4-methyl-2-[(pyrazine-2-carbonyl)-amino]-pentanoylamino}-pentanoylamino)-propionylamino]-cyclopropyl}-2-oxo-acetylamino)-acetic acid

Guidance literature:

Multi-step reaction with 6 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 84 percent / CH₂Cl₂ / 1 h

2.1: NaBH₄ / tetrahydrofuran / 0.5 h / 0 °C

3.1: H₂ / Pd/C / methanol / 0.5 h

4.1: 90 percent / PyBOP; DIEA / dimethylformamide / 4 h / 0 - 20 °C

5.1: 45 percent / Dess-Martin reagent / CH₂Cl₂ / 8 h / 20 °C

6.1: 90 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With sodium tetrahydroborate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; Dess-Martin periodane; ozone; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5.1: Dess-Martin oxidation;

DOI:10.1016/S0960-894X(03)00031-3

upstream raw materials:

(benzyloxycarbonylamino)cyclopropanecarboxylic acid

cyanomethylene triphenylphosphorane

Downstream raw materials:

[2-(1-benzyloxycarbonylamino-cyclopropyl)-2-oxo-acetylamino]-acetic acid tert-butyl ester

(2-{1-[(S)-3-Cyclohexyl-2-((2S,3S)-3-methyl-2-{(S)-4-methyl-2-[(pyrazine-2-carbonyl)-amino]-pentanoylamino}-pentanoylamino)-propionylamino]-cyclopropyl}-2-oxo-acetylamino)-acetic acid tert-butyl ester

(2-{1-[(S)-3-Cyclohexyl-2-((2S,3S)-3-methyl-2-{(S)-4-methyl-2-[(pyrazine-2-carbonyl)-amino]-pentanoylamino}-pentanoylamino)-propionylamino]-cyclopropyl}-2-hydroxy-acetylamino)-acetic acid tert-butyl ester