diphenyl (N-benzyloxycarbonyl-L-alanyl)amino-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)butyl)methanephosphonate

Base Information

• Chemical Name: diphenyl (N-benzyloxycarbonyl-L-alanyl)amino-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)butyl)methanephosphonate
• CAS No.: 695172-06-6
• Molecular Formula: C₃₉H₅₂N₅O₁₀P
• Molecular Weight: 781.843
• Mol file: 695172-06-6.mol

Synonyms:diphenyl (N-benzyloxycarbonyl-L-alanyl)amino-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)butyl)methanephosphonate

Chemical Property of diphenyl (N-benzyloxycarbonyl-L-alanyl)amino-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)butyl)methanephosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diphenyl (N-benzyloxycarbonyl-L-alanyl)amino-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)butyl)methanephosphonate

There total 9 articles about diphenyl (N-benzyloxycarbonyl-L-alanyl)amino-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)butyl)methanephosphonate 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: 26.0%

N-Cbz-Ala (1142-20-7) + C28H41N4O7P → diphenyl (N-benzyloxycarbonyl-L-alanyl)amino-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)butyl)methanephosphonate (695172-06-6)

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;

C₂₈H₄₁N₄O₇P; In N,N-dimethyl-formamide;

DOI:10.1021/jm0499209

Reference yield:

triphenyl phosphite (101-02-0) → diphenyl (N-benzyloxycarbonyl-L-alanyl)amino-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)butyl)methanephosphonate (695172-06-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 45 percent / acetic acid / 2 h / 90 °C

2.1: NH₂NH₂*H₂O / tetrahydrofuran

3.1: 8 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: 26 percent / dimethylformamide

With TEA; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrazine hydrate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm0499209

Reference yield:

5-hydroxypentylamine (2508-29-4) → diphenyl (N-benzyloxycarbonyl-L-alanyl)amino-(4-(N,N'-bis(tert-butyloxycarbonyl)guanyl)butyl)methanephosphonate (695172-06-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine / toluene / 3 h / 125 °C

2.1: 77 percent / oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -78 - 20 °C

3.1: 45 percent / acetic acid / 2 h / 90 °C

4.1: NH₂NH₂*H₂O / tetrahydrofuran

5.1: 8 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: 26 percent / dimethylformamide

With oxalyl dichloride; TEA; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrazine hydrate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Swern oxidation;

DOI:10.1021/jm0499209

upstream raw materials:

N-Cbz-Ala

triphenyl phosphite

5-hydroxypentylamine

5-phthalimido-1-pentanal

Downstream raw materials:

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