N-(9H-fluoren-9-ylmethoxycarbonyl)-O-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valyl}-D-serine benzyl ester

Base Information

• Chemical Name: N-(9H-fluoren-9-ylmethoxycarbonyl)-O-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valyl}-D-serine benzyl ester
• CAS No.: 866832-85-1
• Molecular Formula: C₄₀H₄₄N₂O₈
• Molecular Weight: 680.798
• Mol file: 866832-85-1.mol

Synonyms:N-(9H-fluoren-9-ylmethoxycarbonyl)-O-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valyl}-D-serine benzyl ester

Chemical Property of N-(9H-fluoren-9-ylmethoxycarbonyl)-O-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valyl}-D-serine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(9H-fluoren-9-ylmethoxycarbonyl)-O-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valyl}-D-serine benzyl ester

There total 5 articles about N-(9H-fluoren-9-ylmethoxycarbonyl)-O-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valyl}-D-serine benzyl ester 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: 85.0%

N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valine (866832-83-9) + N-(9H-fluoren-9-ylmethoxycarbonyl)-D-serine benzyl ester (118358-66-0) → N-(9H-fluoren-9-ylmethoxycarbonyl)-O-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valyl}-D-serine benzyl ester (866832-85-1)

Guidance literature:

N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valine; With diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 0.166667h;

N-(9H-fluoren-9-ylmethoxycarbonyl)-D-serine benzyl ester; With dmap; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1021/jo050959a

Reference yield:

Fmoc-D-Ser(Trt)-OH (212688-51-2) → N-(9H-fluoren-9-ylmethoxycarbonyl)-O-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valyl}-D-serine benzyl ester (866832-85-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / caesium carbonate / dimethylformamide / 4 h / 20 °C

2.1: 85 percent / triisopropylsilane; trifluoroacetic acid / CH₂Cl₂ / 0.08 h / 20 °C

3.1: diisopropylcarbodiimide / CH₂Cl₂ / 0.17 h / 20 °C

3.2: 85 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 6 h / 20 °C

With chlorotriisopropylsilane; caesium carbonate; trifluoroacetic acid; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo050959a

Reference yield:

N-(9H-fluoren-9-ylmethoxycarbonyl)-O-trityl-D-serine benzyl ester (866832-84-0) → N-(9H-fluoren-9-ylmethoxycarbonyl)-O-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valyl}-D-serine benzyl ester (866832-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / triisopropylsilane; trifluoroacetic acid / CH₂Cl₂ / 0.08 h / 20 °C

2.1: diisopropylcarbodiimide / CH₂Cl₂ / 0.17 h / 20 °C

2.2: 85 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 6 h / 20 °C

With chlorotriisopropylsilane; trifluoroacetic acid; diisopropyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo050959a

upstream raw materials:

N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-valine

N-(9H-fluoren-9-ylmethoxycarbonyl)-D-serine benzyl ester

Fmoc-D-Ser(Trt)-OH

N-(9H-fluoren-9-ylmethoxycarbonyl)-O-trityl-D-serine benzyl ester