N¹-(tert-butoxycarbonyl)-N⁴-benzyl-N⁹-(2,2,2-trichloro-tert-butoxycarbonyl)-N¹²-(trifluoroacetyl)spermine

Base Information

• Chemical Name: N¹-(tert-butoxycarbonyl)-N⁴-benzyl-N⁹-(2,2,2-trichloro-tert-butoxycarbonyl)-N¹²-(trifluoroacetyl)spermine
• CAS No.: 114491-96-2
• Molecular Formula: C₂₉H₄₄Cl₃F₃N₄O₅
• Molecular Weight: 692.046

Synonyms:N¹-(tert-butoxycarbonyl)-N⁴-benzyl-N⁹-(2,2,2-trichloro-tert-butoxycarbonyl)-N¹²-(trifluoroacetyl)spermine

Chemical Property of N¹-(tert-butoxycarbonyl)-N⁴-benzyl-N⁹-(2,2,2-trichloro-tert-butoxycarbonyl)-N¹²-(trifluoroacetyl)spermine

Chemical Property:

Purity/Quality:

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Technology Process of N¹-(tert-butoxycarbonyl)-N⁴-benzyl-N⁹-(2,2,2-trichloro-tert-butoxycarbonyl)-N¹²-(trifluoroacetyl)spermine

There total 4 articles about N¹-(tert-butoxycarbonyl)-N⁴-benzyl-N⁹-(2,2,2-trichloro-tert-butoxycarbonyl)-N¹²-(trifluoroacetyl)spermine 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: 86.0%

2,2,2-trichloro-1,1-dimethylethoxychloroformate (66270-36-8) + N1-(tert-butoxycarbonyl)-N4-benzyl-N12-(trifluoroacetyl)spermine (114491-95-1) → N1-(tert-butoxycarbonyl)-N4-benzyl-N9-(2,2,2-trichloro-tert-butoxycarbonyl)-N12-(trifluoroacetyl)spermine (114491-96-2)

Guidance literature:

With sodium hydroxide; In diethyl ether; for 0.166667h;

DOI:10.1021/jo00248a037

Reference yield:

N4-Benzyl-N1-(tert-butoxycarbonyl)spermidine (90914-14-0) → N1-(tert-butoxycarbonyl)-N4-benzyl-N9-(2,2,2-trichloro-tert-butoxycarbonyl)-N12-(trifluoroacetyl)spermine (114491-96-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / methanol / 24 h / Ambient temperature

2: 75 percent / NaOH, hydrogen / W-2 Raney nickel / ethanol / 15 h / 2068.6 Torr

3: 82 percent / CH₂Cl₂; benzene / 2 h / 0 °C

4: 86 percent / 0.2 N aq. NaOH / diethyl ether / 0.17 h

With sodium hydroxide; hydrogen; W-2 Raney nickel; In methanol; diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1021/jo00248a037

Reference yield:

1--4-benzyl-4,9-diazadodecanenitrile (114491-93-9) → N1-(tert-butoxycarbonyl)-N4-benzyl-N9-(2,2,2-trichloro-tert-butoxycarbonyl)-N12-(trifluoroacetyl)spermine (114491-96-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / NaOH, hydrogen / W-2 Raney nickel / ethanol / 15 h / 2068.6 Torr

2: 82 percent / CH₂Cl₂; benzene / 2 h / 0 °C

3: 86 percent / 0.2 N aq. NaOH / diethyl ether / 0.17 h

With sodium hydroxide; hydrogen; W-2 Raney nickel; In diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1021/jo00248a037

upstream raw materials:

2,2,2-trichloro-1,1-dimethylethoxychloroformate

N¹-(tert-butoxycarbonyl)-N⁴-benzyl-N¹²-(trifluoroacetyl)spermine

N⁴-Benzyl-N¹-(tert-butoxycarbonyl)spermidine

N¹-(tert-butoxycarbonyl)-N⁴-benzylspermine

Downstream raw materials:

{4-[(3-tert-Butoxycarbonylamino-propyl)-(4-methyl-benzoyl)-amino]-butyl}-[3-(2,2,2-trifluoro-acetylamino)-propyl]-carbamic acid 2,2,2-trichloro-1,1-dimethyl-ethyl ester

{4-[Benzyl-(3-tert-butoxycarbonylamino-propyl)-amino]-butyl}-[3-(4-methyl-benzoylamino)-propyl]-carbamic acid 2,2,2-trichloro-1,1-dimethyl-ethyl ester

(4-{Benzyl-[3-(4-methyl-benzoylamino)-propyl]-amino}-butyl)-[3-(2,2,2-trifluoro-acetylamino)-propyl]-carbamic acid 2,2,2-trichloro-1,1-dimethyl-ethyl ester

{3-[Benzyl-(4-{(4-methyl-benzoyl)-[3-(2,2,2-trifluoro-acetylamino)-propyl]-amino}-butyl)-amino]-propyl}-carbamic acid tert-butyl ester

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