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

Base Information

• Chemical Name: Fmoc-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OH
• CAS No.: 1352788-64-7
• Molecular Formula: C₃₁H₃₁N₃O₆
• Molecular Weight: 541.604
• Mol file: 1352788-64-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about Fmoc-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OH 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:

C16H21N3O4 (1363913-43-2) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OH (1352788-64-7)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 25 ℃; for 21h;

DOI:10.1002/anie.201103315

Reference yield:

Cbz-L-Hpg(Tf)-OBn (1352788-60-3) → Fmoc-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OH (1352788-64-7)

Guidance literature:

Multi-step reaction with 7 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

6: 20% palladium hydroxide on charcoal; hydrogen / methanol; water / 20 h / 25 °C / 3620.13 Torr

7: sodium hydrogencarbonate / N,N-dimethyl-formamide / 21 h / 25 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium periodate; dimethylsulfide; 20% palladium hydroxide on charcoal; ammonium acetate; hydrogen; oxygen; potassium acetate; copper diacetate; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; In 1,3-dioxane; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 5: Chan-Lam coupling;

DOI:10.1002/anie.201103315

Reference yield:

Bn2-L-Hpg(Tf)-OBn (1352788-61-4) → Fmoc-4-(3,3,5,5-tetramethyl-2,6-dioxopiperazin-1-yl)-L-Phg-OH (1352788-64-7)

Guidance literature:

Multi-step reaction with 5 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

4: 20% palladium hydroxide on charcoal; hydrogen / methanol; water / 20 h / 25 °C / 3620.13 Torr

5: sodium hydrogencarbonate / N,N-dimethyl-formamide / 21 h / 25 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium periodate; 20% palladium hydroxide on charcoal; ammonium acetate; hydrogen; oxygen; potassium acetate; copper diacetate; sodium hydrogencarbonate; triethylamine; In 1,3-dioxane; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 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:

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