tetra-O-benzyl danoxamine

Base Information

• Chemical Name: tetra-O-benzyl danoxamine
• CAS No.: 284666-59-7
• Molecular Formula: C₅₅H₇₃N₅O₁₁
• Molecular Weight: 980.212
• Mol file: 284666-59-7.mol

Synonyms:tetra-O-benzyl danoxamine

Chemical Property of tetra-O-benzyl danoxamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tetra-O-benzyl danoxamine

There total 16 articles about tetra-O-benzyl danoxamine 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: 98.0%

succinic acid anhydride (108-30-5) + 1,6,17,29-tetrakis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22,28-pentaazaoctacosane (284666-64-4) → tetra-O-benzyl danoxamine (284666-59-7)

Guidance literature:

With hydrogenchloride; dmap; In dichloromethane; at 20 ℃; for 26.5h; Inert atmosphere;

DOI:10.1021/ol301869x DOI:10.1021/ol301869x

Reference yield:

δ-chlorovaleronitrile (6280-87-1) → tetra-O-benzyl danoxamine (284666-59-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / NaH; NaI / dimethylformamide

2: 91 percent / H₂; NH₃ / Raney Ni / methanol

3: 91 percent / DPPA; Et₃N / acetonitrile / 0 - 20 °C

4: 99 percent / TFA / CH₂Cl₂ / 0.25 h / 20 °C

5: 73 percent / DNAP / pyridine / 20 - 95 °C

6: 94 percent / DPPA; Et₃N / acetonitrile / 0 - 20 °C

7: 76 percent / TFA / CH₂Cl₂ / 0.33 h

8: 61 percent / DMAP / CH₂Cl₂ / 28 h

With dmap; diphenyl-phosphinic acid; ammonia; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; sodium iodide; nickel; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Catalytic hydrogenation / 3: Acylation / 4: Hydrolysis / 5: Acylation / 6: Acylation / 7: Hydrolysis / 8: Acylation;

DOI:10.1021/jo000050m

Reference yield:

tert-butyl N-(benzyloxy)carbamate (79722-21-7) → tetra-O-benzyl danoxamine (284666-59-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / NaH; NaI / dimethylformamide

2: 91 percent / H₂; NH₃ / Raney Ni / methanol

3: 91 percent / DPPA; Et₃N / acetonitrile / 0 - 20 °C

4: 99 percent / TFA / CH₂Cl₂ / 0.25 h / 20 °C

5: 73 percent / DNAP / pyridine / 20 - 95 °C

6: 94 percent / DPPA; Et₃N / acetonitrile / 0 - 20 °C

7: 76 percent / TFA / CH₂Cl₂ / 0.33 h

8: 61 percent / DMAP / CH₂Cl₂ / 28 h

With dmap; diphenyl-phosphinic acid; ammonia; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; sodium iodide; nickel; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Catalytic hydrogenation / 3: Acylation / 4: Hydrolysis / 5: Acylation / 6: Acylation / 7: Hydrolysis / 8: Acylation;

DOI:10.1021/jo000050m

upstream raw materials:

succinic acid anhydride

1,6,17,29-tetrakis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22,28-pentaazaoctacosane

1 ,5-pentanediol

δ-chlorovaleronitrile

Downstream raw materials:

C₇₉H₉₅FN₈O₁₃

C₅₆H₇₅N₅O₁₁

Refernces

• 1、 Wencewicz, Timothy A.,Oliver, Allen G.,Miller, Marvin J.. "Iron(III)-templated macrolactonization of trihydroxamate siderophores". supporting information. p. 4390 - 4393. Retrieved 2013/01/14.