Tyropeptin B

Base Information

• Chemical Name: Tyropeptin B
• CAS No.: 402830-02-8
• Molecular Formula: C28H37N3O6
• Molecular Weight: 511.618
• Mol file: 402830-02-8.mol

Synonyms:(S)-2-[(S)-2-Butyrylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoic acid [1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide;n-butyryl-L-tyrosyl-L-leucyl-DL-tyrosynal;

Chemical Property of Tyropeptin B

Chemical Property:

• Boiling Point: 855.9±65.0 °C(Predicted)
• PKA: 9.83±0.15(Predicted)
• PSA: 144.83000
• Density: 1.196±0.06 g/cm3(Predicted)
• LogP: 3.55520

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tyropeptin B

There total 11 articles about Tyropeptin B 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: 51.0%

n-butyryl-L-tyrosyl-L-leucyl-L-tyrosynol (402832-86-4) → n-butyryl-L-tyrosyl-L-leucyl-DL-tyrosynal (402830-02-8)

Guidance literature:

With pyridine-SO₃ complex; triethylamine; In dimethyl sulfoxide; at 20 ℃; for 1h;

DOI:10.7164/antibiotics.54.1004

Reference yield:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → n-butyryl-L-tyrosyl-L-leucyl-DL-tyrosynal (402830-02-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 3.89 g / Et₃N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH₂Cl₂ / 18 h / 20 °C

2: trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

3: 4.46 g / Et₃N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH₂Cl₂ / 18 h / 20 °C

4: trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

5: 435 mg / Et₃N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / dimethylformamide / 18 h / 20 °C

6: 99 percent / H₂ / 10 percent Pd/C / dimethylformamide / 18 h / 20 °C

7: 51 percent / Et₃N; SO₃*pyridine / dimethylsulfoxide / 1 h / 20 °C

With pyridine-SO₃ complex; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.54.1004

Reference yield:

(S)-tyrosinol hydrochloride (87745-27-5,40829-04-7) → n-butyryl-L-tyrosyl-L-leucyl-DL-tyrosynal (402830-02-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 70 percent / NaOH / dioxane / 3 h / 20 °C

2.1: NaH / dimethylformamide / 0.17 h / 0 °C

2.2: 74 percent / dimethylformamide / 5 h / 20 °C

3.1: trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

4.1: 3.89 g / Et₃N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH₂Cl₂ / 18 h / 20 °C

5.1: trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

6.1: 4.46 g / Et₃N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH₂Cl₂ / 18 h / 20 °C

7.1: trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

8.1: 435 mg / Et₃N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / dimethylformamide / 18 h / 20 °C

9.1: 99 percent / H₂ / 10 percent Pd/C / dimethylformamide / 18 h / 20 °C

10.1: 51 percent / Et₃N; SO₃*pyridine / dimethylsulfoxide / 1 h / 20 °C

With sodium hydroxide; pyridine-SO₃ complex; hydrogen; sodium hydride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.54.1004

upstream raw materials:

n-butyryl-L-tyrosyl-L-leucyl-L-tyrosynol

N-tert-butoxycarbonyl-L-leucine

(S)-tyrosinol hydrochloride

N-(tert-butyloxycarbonyl)-L-tyrosinol

Downstream raw materials:

L-leucine

n-butyryl-L-tyrosyl-L-leucyl-L-tyrosynol

n-butyryl-L-tyrosyl-L-leucyl-D-tyrosynol