Bn₂-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OBn

Base Information

• Chemical Name: Bn₂-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OBn
• CAS No.: 1352788-63-6
• Molecular Formula: C₃₇H₃₉N₃O₄
• Molecular Weight: 589.734
• Mol file: 1352788-63-6.mol

Synonyms:Bn₂-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OBn

Chemical Property of Bn₂-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OBn

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bn₂-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OBn

There total 10 articles about Bn₂-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OBn 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: 78.0%

Bn2-4-dihydroxyborane-L-Phg-OBn (1352788-58-9) + 3,3,5,5-tetramethylpiperazine-2,6-dione (38527-75-2) → Bn2-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OBn (1352788-63-6)

Guidance literature:

With oxygen; copper diacetate; triethylamine; In dimethyl sulfoxide; at 25 ℃; for 336h; Molecular sieve;

DOI:10.1002/anie.201103315

Reference yield:

Cbz-L-Hpg(Tf)-OBn (1352788-60-3) → Bn2-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OBn (1352788-63-6)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethylsulfide; trifluoroacetic acid / 17 h / 25 °C

2: sodium hydrogencarbonate / dimethyl sulfoxide / 25 h / 25 °C

3: 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,3-dioxane / 10 h / 80 °C / Inert atmosphere

4: sodium periodate; ammonium acetate / water; acetone / 48 h / 25 °C

5: oxygen; copper diacetate; triethylamine / dimethyl sulfoxide / 336 h / 25 °C / Molecular sieve

With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium periodate; dimethylsulfide; ammonium acetate; oxygen; potassium acetate; copper diacetate; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; In 1,3-dioxane; water; dimethyl sulfoxide; acetone; 5: Chan-Lam coupling;

DOI:10.1002/anie.201103315

Reference yield:

Bn2-L-Hpg(Tf)-OBn (1352788-61-4) → Bn2-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OBn (1352788-63-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,3-dioxane / 10 h / 80 °C / Inert atmosphere

2: sodium periodate; ammonium acetate / water; acetone / 48 h / 25 °C

3: oxygen; copper diacetate; triethylamine / dimethyl sulfoxide / 336 h / 25 °C / Molecular sieve

With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium periodate; ammonium acetate; oxygen; potassium acetate; copper diacetate; triethylamine; In 1,3-dioxane; water; dimethyl sulfoxide; acetone; 3: Chan-Lam coupling;

DOI:10.1002/anie.201103315

upstream raw materials:

Cbz-L-Hpg(Tf)-OBn

Bn₂-L-Hpg(Tf)-OBn

Bn₂-4-pinacolboryl-L-Phg-OBn

Bn₂-4-dihydroxyborane-L-Phg-OBn

Downstream raw materials:

C₁₆H₂₁N₃O₄

Fmoc-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OH

Fmoc-4-(3,3,5,5-tetramethyl-2,6-dioxo-4-oxylpiperazin-1-yl)-L-Phg-OH