N¹-[3-(3-{3-[3-(4-benzyloxy-phenyl)-2-butylamino-propylamino]-propylamino}-propylamino)-propyl]-butane-1,4-diamine

Base Information

• Chemical Name: N¹-[3-(3-{3-[3-(4-benzyloxy-phenyl)-2-butylamino-propylamino]-propylamino}-propylamino)-propyl]-butane-1,4-diamine
• CAS No.: 196704-39-9
• Molecular Formula: C₃₃H₅₈N₆O
• Molecular Weight: 554.863

Synonyms:N¹-[3-(3-{3-[3-(4-benzyloxy-phenyl)-2-butylamino-propylamino]-propylamino}-propylamino)-propyl]-butane-1,4-diamine

Chemical Property of N¹-[3-(3-{3-[3-(4-benzyloxy-phenyl)-2-butylamino-propylamino]-propylamino}-propylamino)-propyl]-butane-1,4-diamine

Chemical Property:

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Technology Process of N¹-[3-(3-{3-[3-(4-benzyloxy-phenyl)-2-butylamino-propylamino]-propylamino}-propylamino)-propyl]-butane-1,4-diamine

There total 8 articles about N¹-[3-(3-{3-[3-(4-benzyloxy-phenyl)-2-butylamino-propylamino]-propylamino}-propylamino)-propyl]-butane-1,4-diamine 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: 100.0%

{4-[(3-{[3-({3-[3-(4-benzyloxy-phenyl)-2-(tert-butoxycarbonyl-butyl-amino)-propylamino]-propyl}-tert-butoxycarbonyl-amino)-propyl]-tert-butoxycarbonyl-amino}-propyl)-tert-butoxycarbonyl-amino]-butyl}-carbamic acid tert-butyl ester (196704-57-1) → N1-[3-(3-{3-[3-(4-benzyloxy-phenyl)-2-butylamino-propylamino]-propylamino}-propylamino)-propyl]-butane-1,4-diamine (196704-39-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(97)00801-6

Reference yield:

O-benzyl-S-tyrosine (16652-64-5) → N1-[3-(3-{3-[3-(4-benzyloxy-phenyl)-2-butylamino-propylamino]-propylamino}-propylamino)-propyl]-butane-1,4-diamine (196704-39-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 64 percent / SOCl₂ / 4 h / 40 °C

2.1: 67 percent / KF/Celite / acetonitrile / 10 h / Heating

3.1: 100 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

4.1: 94 percent / DIBAL / CH₂Cl₂; hexane / 1 h / 0 °C

5.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.67 h / -50 °C

5.2: 98 percent / Et₃N / CH₂Cl₂ / 0.17 h / -50 - 20 °C

6.1: Na₂SO₄ / ethanol / 24 h / 20 °C

7.1: 225.6 mg / NaBH₄ / ethanol / 12 h / 20 °C

8.1: 100 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With potassium fluoride; sodium tetrahydroborate; thionyl chloride; oxalyl dichloride; Celite; diisobutylaluminium hydride; dimethyl sulfoxide; sodium sulfate; triethylamine; trifluoroacetic acid; In ethanol; hexane; dichloromethane; acetonitrile; 1.1: Esterification / 2.1: Alkylation / 3.1: Acylation / 4.1: Reduction / 5.1: Condensation / 5.2: Elimination / 6.1: Condensation / 7.1: Reduction / 8.1: acidolysis;

DOI:10.1016/S0040-4020(97)00801-6

Reference yield:

O-benzyltyrosine methyl ester (57177-83-0) → N1-[3-(3-{3-[3-(4-benzyloxy-phenyl)-2-butylamino-propylamino]-propylamino}-propylamino)-propyl]-butane-1,4-diamine (196704-39-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 67 percent / KF/Celite / acetonitrile / 10 h / Heating

2.1: 100 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

3.1: 94 percent / DIBAL / CH₂Cl₂; hexane / 1 h / 0 °C

4.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.67 h / -50 °C

4.2: 98 percent / Et₃N / CH₂Cl₂ / 0.17 h / -50 - 20 °C

5.1: Na₂SO₄ / ethanol / 24 h / 20 °C

6.1: 225.6 mg / NaBH₄ / ethanol / 12 h / 20 °C

7.1: 100 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With potassium fluoride; sodium tetrahydroborate; oxalyl dichloride; Celite; diisobutylaluminium hydride; dimethyl sulfoxide; sodium sulfate; triethylamine; trifluoroacetic acid; In ethanol; hexane; dichloromethane; acetonitrile; 1.1: Alkylation / 2.1: Acylation / 3.1: Reduction / 4.1: Condensation / 4.2: Elimination / 5.1: Condensation / 6.1: Reduction / 7.1: acidolysis;

DOI:10.1016/S0040-4020(97)00801-6

upstream raw materials:

{4-[(3-{[3-({3-[3-(4-benzyloxy-phenyl)-2-(tert-butoxycarbonyl-butyl-amino)-propylamino]-propyl}-tert-butoxycarbonyl-amino)-propyl]-tert-butoxycarbonyl-amino}-propyl)-tert-butoxycarbonyl-amino]-butyl}-carbamic acid tert-butyl ester

O-benzyl-S-tyrosine

O-benzyltyrosine methyl ester

(S)-N-butyl-O-benzyltyrosine methyl ester

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