[(S)-2-Carbamoyl-1-(5-hydroxy-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-2-Carbamoyl-1-(5-hydroxy-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester
• CAS No.: 174007-66-0
• Molecular Formula: C₁₇H₂₅N₃O₅
• Molecular Weight: 351.403
• Mol file: 174007-66-0.mol

Synonyms:[(S)-2-Carbamoyl-1-(5-hydroxy-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Chemical Property of [(S)-2-Carbamoyl-1-(5-hydroxy-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-2-Carbamoyl-1-(5-hydroxy-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester

There total 1 articles about [(S)-2-Carbamoyl-1-(5-hydroxy-pentylcarbamoyl)-ethyl]-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: 85.0%

5-hydroxypentylamine (2508-29-4) + N-benzyloxycarbonyl-L-asparagine p-nitrophenyl ester (3256-57-3) → [(S)-2-Carbamoyl-1-(5-hydroxy-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester (174007-66-0)

Guidance literature:

In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/0040-4039(95)01994-S

Reference yield:

[(S)-2-Carbamoyl-1-(5-hydroxy-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester (174007-66-0) → Argiotoxin 636 (105029-41-2,108687-79-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / hydrogen / 10 percent Pd/C / methanol / 16 h / 15 °C / 760 Torr

2: 96 percent / Et₃N / dimethylformamide / 16 h / 20 °C

3: 1.) DMSO, oxalyl chloride / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂/DMSO, -78 deg C

4: 48 percent / glacial HOAc, NaCNBH₃ / methanol / 2 h / 20 °C

5: 80 percent / hydrogen, glacial acetic acid / Pd(OH)2/C / 4 h / 15 °C / 760 Torr

With oxalyl dichloride; hydrogen; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; triethylamine; palladium dihydroxide; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)01994-S

Reference yield:

[(S)-2-Carbamoyl-1-(5-hydroxy-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester (174007-66-0) → C75H88N10O14 (174007-70-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / hydrogen / 10 percent Pd/C / methanol / 16 h / 15 °C / 760 Torr

2: 96 percent / Et₃N / dimethylformamide / 16 h / 20 °C

3: 1.) DMSO, oxalyl chloride / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂/DMSO, -78 deg C

4: 48 percent / glacial HOAc, NaCNBH₃ / methanol / 2 h / 20 °C

With oxalyl dichloride; hydrogen; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)01994-S

upstream raw materials:

5-hydroxypentylamine

N-benzyloxycarbonyl-L-asparagine p-nitrophenyl ester

Downstream raw materials:

Argiotoxin 636

C₇₅H₈₈N₁₀O₁₄

(S)-2-[2-(2,4-Bis-benzyloxy-phenyl)-acetylamino]-N¹-(5-hydroxy-pentyl)-succinamide

(S)-2-[2-(2,4-Bis-benzyloxy-phenyl)-acetylamino]-N¹-(5-oxo-pentyl)-succinamide