Cbz-L-proline-L-alanine methyl ester

Base Information

• Chemical Name: Cbz-L-proline-L-alanine methyl ester
• CAS No.: 51782-87-7
• Molecular Formula: C₁₇H₂₂N₂O₅
• Molecular Weight: 334.372
• Mol file: 51782-87-7.mol

Synonyms:Cbz-L-proline-L-alanine methyl ester

Chemical Property of Cbz-L-proline-L-alanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cbz-L-proline-L-alanine methyl ester

There total 7 articles about Cbz-L-proline-L-alanine methyl 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: 93.0%

L-alanine methyl ester hydrochloride (2491-20-5) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → Cbz-L-proline-L-alanine methyl ester (51782-87-7)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1039/b617217b

Reference yield: 69.7%

L-alanine methyl ester hydrochloride (2491-20-5) + Z-L-Pro-F (133010-21-6) → Cbz-L-proline-L-alanine methyl ester (51782-87-7)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; Ambient temperature;

DOI:10.1021/jo00008a005

Reference yield:

1-ethyl-piperidine (766-09-6) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → Cbz-L-proline-L-alanine methyl ester (51782-87-7)

Guidance literature:

In dichloromethane; ethyl acetate; Petroleum ether;

upstream raw materials:

L-alanine methyl ester hydrochloride

1-benzyl hydrogen (S)-pyrrolidine-1,2-dicarboxylate, compound with dicyclohexylamine (1:1)

Z-L-Pro-F

L-proline

Downstream raw materials:

(S)-2-({(S)-1-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-propionic acid methyl ester

Z-L-Pro-L-Ala-NH-Me

(2S)-2-[({(2S)-1-[(benzyloxy)carbonyl]tetrahydro-1H-pyrrol-2-yl}carbonyl)amino]propanoic acid

(S)-2-({(S)-1-[(S)-2-[(R)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-methyl-benzylsulfanyl)-propionylamino]-3-(4-methyl-benzylsulfanyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-propionic acid methyl ester

Refernces

• 1、 Kon, Kazumasa,Kohari, Yoshihito,Murata, Miki. "Unnatural tripeptide as highly enantioselective organocatalyst for asymmetric aldol reaction of isatins". supporting information. p. 415 - 418. Retrieved 2019/01/05.
• 2、 Carpino, Louis A.,Mansour, El-Sayed M. E.,Sadat-Aalaee, Dean. "tert-Butyloxycarbonyl and Benzyloxycarbonyl Amino Acid Fluorides. New, Stable Rapid-Acting Acylating Agents for Peptide Synthesis". . p. 2611 - 2614. Retrieved 2007/10/02.