Methyl n-[(benzyloxy)carbonyl]phenylalanylleucinate

Base Information

• Chemical Name: Methyl n-[(benzyloxy)carbonyl]phenylalanylleucinate
• CAS No.: 3850-45-1
• Molecular Formula: C24H30N2O5
• Molecular Weight: 426.513
• NSC Number: 111884
• DSSTox Substance ID: DTXSID00296825
• Mol file: 3850-45-1.mol

Synonyms:3850-45-1;methyl n-[(benzyloxy)carbonyl]phenylalanylleucinate;NSC111884;DTXSID00296825;NSC-111884

Chemical Property of Methyl n-[(benzyloxy)carbonyl]phenylalanylleucinate

Chemical Property:

• Vapor Pressure: 3.26E-15mmHg at 25°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 426.21547206
• Heavy Atom Count: 31
• Complexity: 568

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)OC)NC(=O)C(CC1=CC=CC=C1)NC(=O)OCC2=CC=CC=C2

Technology Process of Methyl n-[(benzyloxy)carbonyl]phenylalanylleucinate

There total 35 articles about Methyl n-[(benzyloxy)carbonyl]phenylalanylleucinate 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: 96.0%

N-Cbz-L-Phe (1161-13-3) + methyl (L)-leucinate hydrochloride (7517-19-3) → Cbz-L-Phe-L-Leu-OMe (3850-45-1)

Guidance literature:

With TEA; diphenyl (2,3-dihydro-2-thioxo-3-benzoxazolyl)phosphonate; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1246/bcsj.65.1636

Reference yield: 95.0%

(S)-Leu-OMe (2666-93-5) + N-Cbz-L-Phe (1161-13-3) → Cbz-L-Phe-L-Leu-OMe (3850-45-1)

Guidance literature:

With 1c-CPC(Th); In acetonitrile; at 37 ℃; for 48h;

DOI:10.1021/ja00027a068

Reference yield: 94.5%

methyl (L)-leucinate hydrochloride (7517-19-3) + Z-DL-Phe-OH (3588-57-6) → Cbz-L-Phe-L-Leu-OMe (3850-45-1)

Guidance literature:

With 4-methyl-morpholine; DMT*brucine tetrafluoroborate; brucine; In acetonitrile; at 0 - 20 ℃; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ol802691x

upstream raw materials:

N-Benzyloxycarbonyl-L-phenylalanin-

methyl (L)-leucinate hydrochloride

N-Cbz-L-Phe

(S)-Leu-OMe

Downstream raw materials:

Ac-(S)-Phe-(S)-Leu-OMe

(2S)-2--4-methylpentan-1-al

N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-(R)alanyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester

(S)-2-{(S)-2-[2-((R)-2-{2-Benzyloxycarbonylamino-3-[4-(toluene-4-sulfonyloxy)-phenyl]-propionylamino}-propionylamino)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

Refernces

• 1、 Pehere, Ashok D.,Nguyen, Steven,Garlick, Sarah K.,Wilson, Danny W.,Hudson, Irene,Sykes, Matthew J.,Morton, James D.,Abell, Andrew D.. "Tripeptide analogues of MG132 as protease inhibitors". supporting information. p. 436 - 441. Retrieved 2019/01/04.
• 2、 Zhao, De-Yin,Zhang, Ming-Xia,Dong, Xiao-Wu,Hu, Yong-Zhou,Dai, Xiao-Yan,Wei, Xiaoyi,Hider, Robert C.,Zhang, Jin-Chao,Zhou, Tao. "Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors". supporting information. p. 3103 - 3108. Retrieved 2016/06/13.