diphenyl 1-((N-benzyloxycarbonyl-L-alanyl)amino)-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)phenyl)ethanephosphonate

Base Information

• Chemical Name: diphenyl 1-((N-benzyloxycarbonyl-L-alanyl)amino)-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)phenyl)ethanephosphonate
• CAS No.: 695172-09-9
• Molecular Formula: C₄₂H₅₀N₅O₁₀P
• Molecular Weight: 815.86

Synonyms:diphenyl 1-((N-benzyloxycarbonyl-L-alanyl)amino)-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)phenyl)ethanephosphonate

Chemical Property of diphenyl 1-((N-benzyloxycarbonyl-L-alanyl)amino)-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)phenyl)ethanephosphonate

Chemical Property:

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Technology Process of diphenyl 1-((N-benzyloxycarbonyl-L-alanyl)amino)-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)phenyl)ethanephosphonate

There total 8 articles about diphenyl 1-((N-benzyloxycarbonyl-L-alanyl)amino)-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)phenyl)ethanephosphonate 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: 41.0%

N-Cbz-Ala (1142-20-7) + diphenyl 1-amino-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanidino)phenyl)ethyl-phosphonate (913239-29-9) → diphenyl 1-((N-benzyloxycarbonyl-L-alanyl)amino)-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)phenyl)ethanephosphonate (695172-09-9)

Guidance literature:

N-Cbz-Ala; With TEA; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

diphenyl 1-amino-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanidino)phenyl)ethyl-phosphonate; In N,N-dimethyl-formamide;

DOI:10.1021/jm0499209

Reference yield:

4-aminobenzenemethanol (623-04-1) → diphenyl 1-((N-benzyloxycarbonyl-L-alanyl)amino)-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)phenyl)ethanephosphonate (695172-09-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: aq. NaOH / dioxane / 20 °C

2.1: 80 percent / Dess-Martin periodane / CH₂Cl₂ / 3 h / 20 °C

3.1: 30 percent / Cu(OTf)2 / CH₂Cl₂ / 4 h / 20 °C

4.1: TFA / CH₂Cl₂ / 3 h / 20 °C

5.1: 65 percent / TEA / acetonitrile / 20 °C

6.1: H₂ / Pd/C / methanol / 8 h / 20 °C

7.1: 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium*BF₄; TEA / dimethylformamide / 0.17 h / 20 °C

7.2: 41 percent / dimethylformamide

With sodium hydroxide; TEA; hydrogen; copper(II) bis(trifluoromethanesulfonate); Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Dess-Martin oxidation;

DOI:10.1021/jm0499209

Reference yield:

4-((tert-butoxycarbonyl)amino)benzaldehyde (144072-30-0) → diphenyl 1-((N-benzyloxycarbonyl-L-alanyl)amino)-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)phenyl)ethanephosphonate (695172-09-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 30 percent / Cu(OTf)2 / CH₂Cl₂ / 4 h / 20 °C

2.1: TFA / CH₂Cl₂ / 3 h / 20 °C

3.1: 65 percent / TEA / acetonitrile / 20 °C

4.1: H₂ / Pd/C / methanol / 8 h / 20 °C

5.1: 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium*BF₄; TEA / dimethylformamide / 0.17 h / 20 °C

5.2: 41 percent / dimethylformamide

With TEA; hydrogen; copper(II) bis(trifluoromethanesulfonate); O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm0499209

upstream raw materials:

N-Cbz-Ala

diphenyl 1-amino-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanidino)phenyl)ethyl-phosphonate

4-aminobenzenemethanol

4-((tert-butoxycarbonyl)amino)benzaldehyde

Downstream raw materials:

diphenyl 1-(((N-benzyloxycarbonyl-O-tert-butyl-D-seryl)-L-alanyl)amino)-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)phenyl)ethanephosphonate

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