N-(benzyloxycarbonyl)-L-valine N-hydroxy-5-norbornene-2,3-dicarboximide ester

Base Information

• Chemical Name: N-(benzyloxycarbonyl)-L-valine N-hydroxy-5-norbornene-2,3-dicarboximide ester
• CAS No.: 53666-01-6
• Molecular Formula: C₂₂H₂₄N₂O₆
• Molecular Weight: 412.442
• Mol file: 53666-01-6.mol

Synonyms:N-(benzyloxycarbonyl)-L-valine N-hydroxy-5-norbornene-2,3-dicarboximide ester

Chemical Property of N-(benzyloxycarbonyl)-L-valine N-hydroxy-5-norbornene-2,3-dicarboximide ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(benzyloxycarbonyl)-L-valine N-hydroxy-5-norbornene-2,3-dicarboximide ester

There total 7 articles about N-(benzyloxycarbonyl)-L-valine N-hydroxy-5-norbornene-2,3-dicarboximide 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: 99.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester isopropenyl ester (137283-63-7) → N-(benzyloxycarbonyl)-L-valine N-hydroxy-5-norbornene-2,3-dicarboximide ester (53666-01-6)

Guidance literature:

With dmap; In acetonitrile; for 4h; Ambient temperature;

DOI:10.1055/s-1991-26545

Reference yield:

N-hydroxy-5-norbornene-2,3-dicarboximide (21715-90-2) → N-(benzyloxycarbonyl)-L-valine N-hydroxy-5-norbornene-2,3-dicarboximide ester (53666-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Et₃N / acetonitrile; acetone / 0 °C

2: 99 percent / DMAP / acetonitrile / 4 h / Ambient temperature

With dmap; triethylamine; In acetone; acetonitrile;

DOI:10.1055/s-1991-26545

Reference yield:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + N,N'-dinorborneno oxallate(DPO) (89028-39-7) → (S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid (1S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester (53666-01-6)

Guidance literature:

With pyridine; In acetonitrile; for 5h;

DOI:10.1016/S0040-4039(00)85923-7

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

N,N'-dinorborneno oxallate(DPO)

N-hydroxy-5-norbornene-2,3-dicarboximide

Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester isopropenyl ester

Downstream raw materials:

Boc-GlyIleValGlu(OBut)Gln(Mbh)-OH

Z-IleValGlu(OBut)-OH

N-(benzyloxycarbonyl)-L-valyl-D-isoglutamine t-butyl ester

Z-Val-γAbu-OBzl

Refernces

• 1、 Henklein, Peter,Ott, Tilmann,Jaehrling, Renate,Scharfenberg, Peter,Heyne, Hans-Ulrich,Niedrich, Hartmut. "Synthese von Carbonsaeure-norborn-5-en-2,3-dicarboximestern". . p. 289 - 290. Retrieved 2007/10/02.
• 2、 Takeda, Kazuyoshi,Sawada, Izumi,Suzuki, Akira,Ogura, Haruo. "A Convenient Synthesis of Peptide Using Oxallates". . p. 4451 - 4454. Retrieved 2007/10/02.