N⁶,N¹⁰-dibenzyl-N¹⁶-benzyloxycarboyl-N¹-[N-(tert-butoxycarbonyl)-L-phenylalanine]-6,10-diaza-1,16-diaminohexadecane

Base Information

• Chemical Name: N⁶,N¹⁰-dibenzyl-N¹⁶-benzyloxycarboyl-N¹-[N-(tert-butoxycarbonyl)-L-phenylalanine]-6,10-diaza-1,16-diaminohexadecane
• CAS No.: 204692-31-9
• Molecular Formula: C₅₀H₆₉N₅O₅
• Molecular Weight: 820.128

Synonyms:N⁶,N¹⁰-dibenzyl-N¹⁶-benzyloxycarboyl-N¹-[N-(tert-butoxycarbonyl)-L-phenylalanine]-6,10-diaza-1,16-diaminohexadecane

Chemical Property of N⁶,N¹⁰-dibenzyl-N¹⁶-benzyloxycarboyl-N¹-[N-(tert-butoxycarbonyl)-L-phenylalanine]-6,10-diaza-1,16-diaminohexadecane

Chemical Property:

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Technology Process of N⁶,N¹⁰-dibenzyl-N¹⁶-benzyloxycarboyl-N¹-[N-(tert-butoxycarbonyl)-L-phenylalanine]-6,10-diaza-1,16-diaminohexadecane

There total 12 articles about N⁶,N¹⁰-dibenzyl-N¹⁶-benzyloxycarboyl-N¹-[N-(tert-butoxycarbonyl)-L-phenylalanine]-6,10-diaza-1,16-diaminohexadecane 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: 95.0%

N-t-butoxycarbonyl-L-phenylalanine 4-nitrophenyl ester (7535-56-0) + N6,N10-dibenzyl-N16-benzyloxycarboyl-6,10-diaza-1,16-diaminohexadecane (204689-75-8) → N6,N10-dibenzyl-N16-benzyloxycarboyl-N1-[N-(tert-butoxycarbonyl)-L-phenylalanine]-6,10-diaza-1,16-diaminohexadecane (204692-31-9)

Guidance literature:

In dichloromethane; for 16h;

DOI:10.1023/A:1011988317683

Reference yield:

5-tert-butoxycarbonylamino-1-aminopentane (51644-96-3) → N6,N10-dibenzyl-N16-benzyloxycarboyl-N1-[N-(tert-butoxycarbonyl)-L-phenylalanine]-6,10-diaza-1,16-diaminohexadecane (204692-31-9)

Guidance literature:

Multi-step reaction with 11 steps

1: MgSO₄ / methanol / 3 h

2: NaBH₄ / methanol / 19 h / Heating

3: 83.1 percent / 50 percent KF/Celite / acetonitrile / 15 h / Heating

4: 85.5 percent / N₂H₄ / methanol / 15 h / Heating

5: MgSO₄ / methanol

6: NaBH₄ / methanol / Heating

7: 65 percent / 50 percent KF/Celite / acetonitrile / Heating

8: 90 percent / N₂H₄ / methanol / Heating

9: 87 percent / triethylamine / CHCl₃ / 69 h

10: 98 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

11: 95 percent / CH₂Cl₂ / 16 h

With potassium fluoride; sodium tetrahydroborate; Celite; magnesium sulfate; triethylamine; trifluoroacetic acid; hydrazine; In methanol; dichloromethane; chloroform; acetonitrile; 1: Condensation / 2: Reduction / 3: Alkylation / 4: dephthaloylation / 5: Condensation / 6: Reduction / 7: Alkylation / 8: dephthaloylation / 9: Condensation / 10: Boc group cleavage / 11: Condensation;

DOI:10.1023/A:1011988317683

Reference yield:

N1-benzyl-N5-(tert-butoxycarbonyl)-1,5-diaminopentane (122631-98-5) → N6,N10-dibenzyl-N16-benzyloxycarboyl-N1-[N-(tert-butoxycarbonyl)-L-phenylalanine]-6,10-diaza-1,16-diaminohexadecane (204692-31-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 83.1 percent / 50 percent KF/Celite / acetonitrile / 15 h / Heating

2: 85.5 percent / N₂H₄ / methanol / 15 h / Heating

3: MgSO₄ / methanol

4: NaBH₄ / methanol / Heating

5: 65 percent / 50 percent KF/Celite / acetonitrile / Heating

6: 90 percent / N₂H₄ / methanol / Heating

7: 87 percent / triethylamine / CHCl₃ / 69 h

8: 98 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

9: 95 percent / CH₂Cl₂ / 16 h

With potassium fluoride; sodium tetrahydroborate; Celite; magnesium sulfate; triethylamine; trifluoroacetic acid; hydrazine; In methanol; dichloromethane; chloroform; acetonitrile; 1: Alkylation / 2: dephthaloylation / 3: Condensation / 4: Reduction / 5: Alkylation / 6: dephthaloylation / 7: Condensation / 8: Boc group cleavage / 9: Condensation;

DOI:10.1023/A:1011988317683

upstream raw materials:

N-t-butoxycarbonyl-L-phenylalanine 4-nitrophenyl ester

N⁶,N¹⁰-dibenzyl-N¹⁶-benzyloxycarboyl-6,10-diaza-1,16-diaminohexadecane

5-tert-butoxycarbonylamino-1-aminopentane

N¹-benzyl-N⁵-(tert-butoxycarbonyl)-1,5-diaminopentane

Downstream raw materials:

N⁶,N¹⁰-dibenzyl-N¹⁶-benzyloxycarboyl-N¹-(L-phenylalanine)-6,10-diaza-1,16-diaminohexadecane

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