21-amino-5,16-bis(benzyloxy)-4,12,15-trioxo-5,11,16-triazaheneicosanoic acid

Base Information

• Chemical Name: 21-amino-5,16-bis(benzyloxy)-4,12,15-trioxo-5,11,16-triazaheneicosanoic acid
• CAS No.: 129245-25-6
• Molecular Formula: C₃₂H₄₆N₄O₇
• Molecular Weight: 598.74
• Mol file: 129245-25-6.mol

Synonyms:21-amino-5,16-bis(benzyloxy)-4,12,15-trioxo-5,11,16-triazaheneicosanoic acid

Chemical Property of 21-amino-5,16-bis(benzyloxy)-4,12,15-trioxo-5,11,16-triazaheneicosanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 21-amino-5,16-bis(benzyloxy)-4,12,15-trioxo-5,11,16-triazaheneicosanoic acid

There total 18 articles about 21-amino-5,16-bis(benzyloxy)-4,12,15-trioxo-5,11,16-triazaheneicosanoic 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: 92.0%

C32H44N6O7 → 21-amino-5,16-bis(benzyloxy)-4,12,15-trioxo-5,11,16-triazaheneicosanoic acid (129245-25-6)

Guidance literature:

C₃₂H₄₄N₆O₇; With triphenylphosphine; In tetrahydrofuran; at 80 ℃; for 1h;

With water; In tetrahydrofuran; at 80 ℃; for 1h;

DOI:10.1002/ejoc.202000439

Reference yield: 65.0%

5,16-bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid (129245-24-5) → 21-amino-5,16-bis(benzyloxy)-4,12,15-trioxo-5,11,16-triazaheneicosanoic acid (129245-25-6)

Guidance literature:

With ammonium hydroxide; nickel; In methanol; at 0 ℃; for 3h; under 2844.3 - 2999.5 Torr;

DOI:10.1016/S0040-4020(01)81074-7

Reference yield:

tert-butyl N-(benzyloxy)carbamate (79722-21-7) → 21-amino-5,16-bis(benzyloxy)-4,12,15-trioxo-5,11,16-triazaheneicosanoic acid (129245-25-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) sodium iodide, 80percent sodium hydride / 1.) DMF, 15 min, 2.) DMF, 80 - 85 deg C, 4 h

2: 83 percent / conc. NH₄OH, NH₃ / Raney nickel / methanol / 3.5 h / 0 °C / 2844.3 - 2999.5 Torr

3: 65 percent / 4-dimethylaminopyridine, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 1.) 0 deg C, 45 min, 2.) room temp., 19 h

4: 83 percent / TFA / 0.33 h / Ambient temperature

5: 96 percent / pyridine / 1.5 h / 106 °C

6: 65 percent / conc. NH₄OH, NH₃ / Raney nickel / methanol / 3 h / 0 °C / 2844.3 - 2999.5 Torr

With dmap; ammonium hydroxide; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium iodide; nickel; In pyridine; methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)81074-7

upstream raw materials:

5,16-bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid

δ-chlorovaleronitrile

O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine

tert-butyl N-(benzyloxy)carbamate

Downstream raw materials:

bisucaberin

6,17-bis(benzyloxy)-1,6,12,17-tetraazacyclodocosane-2,5,13,16-tetrone