N-(benzyloxycarbonyl)-D-phenylalaninylprolylsarcosine tert-butyl ester

Base Information

• Chemical Name: N-(benzyloxycarbonyl)-D-phenylalaninylprolylsarcosine tert-butyl ester
• CAS No.: 158629-40-4
• Molecular Formula: C₂₉H₃₇N₃O₆
• Molecular Weight: 523.629
• Mol file: 158629-40-4.mol

Synonyms:N-(benzyloxycarbonyl)-D-phenylalaninylprolylsarcosine tert-butyl ester

Chemical Property of N-(benzyloxycarbonyl)-D-phenylalaninylprolylsarcosine tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(benzyloxycarbonyl)-D-phenylalaninylprolylsarcosine tert-butyl ester

There total 4 articles about N-(benzyloxycarbonyl)-D-phenylalaninylprolylsarcosine tert-butyl 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:

Cbz-D-Phe (2448-45-5) + [Methyl-((S)-pyrrolidine-2-carbonyl)-amino]-acetic acid tert-butyl ester (63219-23-8) → N-(benzyloxycarbonyl)-D-phenylalaninylprolylsarcosine tert-butyl ester (158629-40-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at -10 ℃; for 3h; Yield given;

DOI:10.1021/ja00097a003

Reference yield:

sarcosine tert-butyl ester (5616-81-9) → N-(benzyloxycarbonyl)-D-phenylalaninylprolylsarcosine tert-butyl ester (158629-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

2: H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr

3: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

With hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja00097a003

Reference yield:

N-(benzyloxycarbonyl)prolylsarcosine tert-butyl ester (5616-82-0) → N-(benzyloxycarbonyl)-D-phenylalaninylprolylsarcosine tert-butyl ester (158629-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr

2: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

With hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja00097a003

upstream raw materials:

Cbz-D-Phe

[Methyl-((S)-pyrrolidine-2-carbonyl)-amino]-acetic acid tert-butyl ester

sarcosine tert-butyl ester

N-(benzyloxycarbonyl)prolylsarcosine tert-butyl ester

Downstream raw materials:

N-(benzyloxycarbonyl)threonyl-D-phenylalaninylprolylsarcosine tert-butyl ester

N-(benzyloxycarbonyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone

O-(tert-butoxycarbonyl)-N-methylvalyl-N-(benzyloxycarbonyl)threonyl-D-phenylalaninylprolylsarcosine tert-butyl ester

(3-(benzyloxy)-4-methyl-2-nitrobenzoyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone