Methyl n-[(benzyloxy)carbonyl]valyltyrosinate

Base Information

• Chemical Name: Methyl n-[(benzyloxy)carbonyl]valyltyrosinate
• CAS No.: 15149-72-1
• Molecular Formula: C23H28 N2 O6
• Molecular Weight: 428.485
• NSC Number: 89592
• DSSTox Substance ID: DTXSID50293445
• Mol file: 15149-72-1.mol

Synonyms:methyl n-[(benzyloxy)carbonyl]valyltyrosinate;15149-72-1;Z-Val-Tyr methyl ester;methyl 3-(4-hydroxyphenyl)-2-[[3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoate;NSC89592;DTXSID50293445;NSC-89592;AKOS003389445;FT-0637192;methyl 2-[(2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoyl)amino]-3-(4-hydroxyphenyl)propanoate

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

Chemical Property:

• Vapor Pressure: 9.66E-18mmHg at 25°C
• Melting Point: 155.5-156℃
• Boiling Point: 654.7 °C at 760 mmHg
• PKA: 9.75±0.15(Predicted)
• Flash Point: 349.7 °C
• PSA: 113.96000
• Density: 1.214 g/cm³
• LogP: 3.32530
• Storage Temp.: −20°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 428.19473662
• Heavy Atom Count: 31
• Complexity: 583

Purity/Quality:

99% ^*data from raw suppliers

Z-Val-Tyr methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 10 articles about Methyl n-[(benzyloxy)carbonyl]valyltyrosinate 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)-N-(benzyloxycarbonyl)valine (1149-26-4) + L-Tyr-OMe (1080-06-4) → N-(N-benzyloxycarbonyl-L-valyl)-L-tyrosine methyl ester (15149-72-1)

Guidance literature:

With triethylamine; betamethasone sodium phosphate; In N,N-dimethyl-formamide; for 3h; Ambient temperature;

DOI:10.1016/S0040-4039(00)94888-3

Reference yield: 93.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + L-tyrosine methyl ester HCl (3417-91-2) → N-(N-benzyloxycarbonyl-L-valyl)-L-tyrosine methyl ester (15149-72-1)

Guidance literature:

With triethylamine; 2-Pyridon-1-yl diphenyl phosphate; In N,N-dimethyl-formamide; for 3h; Ambient temperature;

DOI:10.1039/c39860000719

Reference yield: 62.0%

methanol (67-56-1) + N-benzyloxycarbonylvalyltyrosine hydrazide (5992-90-5) → N-(N-benzyloxycarbonyl-L-valyl)-L-tyrosine methyl ester (15149-72-1)

Guidance literature:

With Amberlyst 15; at 60 ℃; for 2h;

DOI:10.1021/jo00339a019

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

L-Tyr-OMe

2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate

L-tyrosine methyl ester HCl

Downstream raw materials:

N-benzyloxycarbonyl-L-valyl=>L-tyrosyl=>L-valyl=>L-histidyl=>L-prolyl=>L-phenylalanine-methyl ester

N-benzyloxycarbonyl-L-valyl=>L-tyrosyl=>L-isoleucyl=>L-histidine-methyl ester

N-benzyloxycarbonyl-valyl->-tyrosyl->-valyl->-histidine methyl ester

N²-benzyloxycarbonyl-L-asparaginyl=>N^ω-nitro-L-arginyl=>L-valyl=>L-tyrosine methyl ester

Refernces

• 1、 Lee, Hee-Yoon,Sohn, Jeong-Hun,Kwon, Byoung-Mog. "Development of tripeptidyl farnesyltransferase inhibitors.". . p. 1599 - 1602. Retrieved 2007/10/03.
• 2、 Kim, Sunggak,Kim, Sung Soo. "2-Pyridon-1-yl Diphenyl Phosphate. A Useful New Reagent for the Synthesis of Amides and Peptides". . p. 719. Retrieved 2007/10/02.