5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid

Base Information

• Chemical Name: 5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid
• CAS No.: 153492-12-7
• Molecular Formula: C₂₁H₃₂N₂O₆
• Molecular Weight: 408.495
• Mol file: 153492-12-7.mol

Synonyms:5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid

Chemical Property of 5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid

There total 16 articles about 5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic 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: 90.0%

N-Benzyloxy-N-(5-tert-butoxycarbonylamino-pentyl)-succinamic acid methyl ester (153492-10-5) → 5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid (153492-12-7)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran;

DOI:10.1021/jo00079a007

Reference yield: 88.0%

succinic acid anhydride (108-30-5) + 1-<(tert-Butoxycarbonyl)amino>-5-<(benzyloxy)amino>pentane (153492-09-2) → 5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid (153492-12-7)

Guidance literature:

With pyridine; at 80 - 86 ℃; for 1.5h;

DOI:10.1021/jo00106a022

Reference yield:

N-<(2,2,2-trichloroethoxy)carbonyl>-O-benzylhydroxylamine (90195-00-9) → 5-(Benzyloxy)-11-(tert-butoxycarbonyl)-4-oxo-5,11-diazaundecanoic acid (153492-12-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 95.5 percent / Ph₃P, DEAD / tetrahydrofuran / 16 h / Ambient temperature

2: Zn, AcOH / tetrahydrofuran / 1 h / Ambient temperature

With acetic acid; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jo00079a007

upstream raw materials:

succinic acid anhydride

1-<(tert-Butoxycarbonyl)amino>-5-<(trichloroethoxycarbonyl)(benzyloxy)amino>pentane

N-Benzyloxy-N-(5-tert-butoxycarbonylamino-pentyl)-succinamic acid methyl ester

1-<(tert-Butoxycarbonyl)amino>-5-<(benzyloxy)amino>pentane

Downstream raw materials:

5,16-Bis(benzyloxy)-22-(tert-butoxycarbonyl)-4,12,15-trioxo-5,11,16,22-tetraazadocosanoic acid

1-(tert-Butoxycarbonyl)-7,18,29-tris(benzyloxy)-8,11,19,22-tetraoxo-1,7,12,18,23,29-hexaazanonacosane

1-(tert-Butoxycarbonyl)-7,18,29-tris(benzyloxy)-8,11,19,22,30-pentaoxo-1,7,12,18,23,29-hexaazahentriacontane

Refernces

• 1、 -. "Method for preparing desferrioxamine B and homologs thereof". . . Retrieved 2008/06/13.
• 2、 Ghosh, Arun,Miller, Marvin J.. "Synthesis of Novel Citrate-Based Siderophores and Siderophore-β-Lactam Conjugates. Iron Transport-Mediated Drug Delivery Systems". . p. 7652 - 7659. Retrieved 2007/10/02.