n-butyl N-benzyloxycarbonylalaninoate

Base Information

• Chemical Name: n-butyl N-benzyloxycarbonylalaninoate
• CAS No.: 117402-81-0
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.336
• Mol file: 117402-81-0.mol

Synonyms:n-butyl N-benzyloxycarbonylalaninoate

Chemical Property of n-butyl N-benzyloxycarbonylalaninoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of n-butyl N-benzyloxycarbonylalaninoate

There total 6 articles about n-butyl N-benzyloxycarbonylalaninoate 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: 95.0%

(S)-2-benzyloxycarbonylamino-propionic acid methyl ester (28819-05-8) + butan-1-ol (71-36-3) → n-butyl N-benzyloxycarbonylalaninoate (117402-81-0)

Guidance literature:

With C₁₂H₆F₁₈O₁₃Zn₄; In di-isopropyl ether; for 18h; Reflux; Inert atmosphere;

DOI:10.1055/s-0031-1290096

Reference yield: 80.0%

N-benzyloxycarbonylalanine (4132-86-9,26607-51-2,1142-20-7) + butan-1-ol (71-36-3) → N-benzyloxycarbonyl-D-alanine (26607-51-2) + n-butyl N-benzyloxycarbonylalaninoate (117402-81-0)

Guidance literature:

With citrate buffer; DL-cysteine hydrochloride; papain; at 50 ℃; for 24h;

Reference yield: 68.0%

N-Cbz-Ala (1142-20-7) + butan-1-ol (71-36-3) → n-butyl N-benzyloxycarbonylalaninoate (117402-81-0)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 16h; Reflux; Inert atmosphere;

DOI:10.1039/c1ob06074k

upstream raw materials:

N-benzyloxycarbonylalanine

butan-1-ol

N-Cbz-Ala

Cbz-alanine ethyl ester

Downstream raw materials:

N-Cbz-Ala

Z-(S)-Ala-(S)-Leu-NH₂

(S,E)-n-butyl 2-methyl-2-(pyrrolidin-1-yl)-4-(p-toluenesulfonyl)but-3-enoate

(S)-butyl 2-aminopropanoate

Refernces

• 1、 Maegawa, Yusuke,Agura, Kazushi,Hayashi, Yukiko,Ohshima, Takashi,Mashima, Kazushi. "Transesterification of α-amino esters catalyzed by a tetranuclear zinc cluster: Zn4(OCOCF3)6O". supporting information; experimental part. p. 137 - 141. Retrieved 2012/02/03.
• 2、 Watanabe, Keiichi,Yoshida, Takashi,Ueji, Shin-Ichi. "The role of conformational flexibility of enzymes in the discrimination between amino acid and ester substrates for the subtilisin-catalyzed reaction in organic solvents". . p. 504 - 515. Retrieved 2007/10/03.