cyclo(tyrosylarginyl)

Base Information

• Chemical Name: cyclo(tyrosylarginyl)
• CAS No.: 81205-31-4
• Molecular Formula: C15H21 N5 O3
• Molecular Weight: 319.36
• Mol file: 81205-31-4.mol

Synonyms:Guanidine,[3-[5-[(4-hydroxyphenyl)methyl]-3,6-dioxo-2-piperazinyl]propyl]-, (2S-cis)-;Cyclic kyotorphin; Cyclo(L-tyrosyl-L-arginine); NSC 357032

Chemical Property of cyclo(tyrosylarginyl)

Chemical Property:

• PSA: 142.83000
• Density: 1.47g/cm³
• LogP: 1.02970

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cyclo(tyrosylarginyl)

There total 8 articles about cyclo(tyrosylarginyl) 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: 92.0%

cyclo<-Tyr(Bzl)-Arg-> (83541-40-6) → cyclo(-Tyr-Arg-) (78172-86-8,81205-31-4,81205-32-5,81205-33-6,81205-34-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; for 16h;

DOI:10.1248/cpb.29.3403

Reference yield:

t-butyloxycarbonyl-L-arginine (13726-76-6,78603-12-0) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → cycloarginyltyrosine (81205-31-4)

Guidance literature:

L-tyrosine; With dmap; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

With trifluoroacetic acid; In dichloromethane; for 0.5h;

t-butyloxycarbonyl-L-arginine; Further stages;

DOI:10.1016/j.bmc.2018.11.042

Reference yield:

D-arginine (157-06-2,25212-18-4) → cyclo(-D-Tyr-D-Arg-) (78172-86-8,81205-31-4,81205-32-5,81205-33-6,81205-34-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / SOCl₂

2: DCC, HOBt, TEA / dimethylformamide / 20 h / 0 - 5 °C

3: 4N HCl / dioxane / 0.5 h

4: 1.) AcOH, 2.) H₂ / 2.) 10percent Pd/C

With hydrogenchloride; thionyl chloride; TEA; hydrogen; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.29.3403

upstream raw materials:

t-butyloxycarbonyl-L-arginine

L-tyrosine

H-D-Tyr(Br-Z)-D-Arg-OMe*2HCl

D-arginine

Downstream raw materials:

C.<-Tyr-Arg(DHCH)->.CH3COOH

Refernces

• 1、 Sasaki,Akutsu,Suzuki,Sakurada,Kisara. "Structure and analgesic activity relationship of cyclo Tyrosyl Arginyl and its three stereoisomers". . p. 3403 - 3406. Retrieved 2007/10/02.