(4-{(R)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester

Base Information

• Chemical Name: (4-{(R)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester
• CAS No.: 914459-78-2
• Molecular Formula: C₃₄H₅₄N₅O₇P
• Molecular Weight: 675.806
• Mol file: 914459-78-2.mol

Synonyms:(4-{(R)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester

Chemical Property of (4-{(R)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-{(R)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester

There total 6 articles about (4-{(R)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-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: 37.0%

{4-[2-[1-(2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-benzyl}-phosphonic acid di-tert-butyl ester (914459-76-0) → (4-{(R)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester (914459-78-2) + (4-{(S)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester (914459-77-1)

Guidance literature:

With piperidine; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2006.08.004

Reference yield:

2-amino-N1-pent-4-ynyl-succinamide (914459-74-8) → (4-{(R)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester (914459-78-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide*HCl / dimethylformamide / 12 h / 20 °C

2: piperidine / acetonitrile / 2 h / 20 °C

3: 1-hydroxybenzotriazole; EDCI*HCl / dimethylformamide / 12 h / 20 °C

4: 38 percent / piperidine / acetonitrile / 2 h / 20 °C

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

DOI:10.1016/j.bmcl.2006.08.004

Reference yield:

(2-carbamoyl-1-pent-4-ynylcarbamoyl-ethyl)-carbamic acid tert-butyl ester (914459-73-7) → (4-{(R)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester (914459-78-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

2: 84 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide*HCl / dimethylformamide / 12 h / 20 °C

3: piperidine / acetonitrile / 2 h / 20 °C

4: 1-hydroxybenzotriazole; EDCI*HCl / dimethylformamide / 12 h / 20 °C

5: 38 percent / piperidine / acetonitrile / 2 h / 20 °C

With piperidine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmcl.2006.08.004

upstream raw materials:

{4-[2-[1-(2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-benzyl}-phosphonic acid di-tert-butyl ester

2-amino-N¹-pent-4-ynyl-succinamide

(2-carbamoyl-1-pent-4-ynylcarbamoyl-ethyl)-carbamic acid tert-butyl ester

[1-(2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Downstream raw materials:

(4-{(R)-2-(2-Azido-acetylamino)-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester