methyl N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)-2-pyridylcarbonyl]-L-histidinate

Base Information

• Chemical Name: methyl N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)-2-pyridylcarbonyl]-L-histidinate
• CAS No.: 209467-29-8
• Molecular Formula: C₃₂H₃₄N₆O₇
• Molecular Weight: 614.658
• Mol file: 209467-29-8.mol

Synonyms:

Chemical Property of methyl N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)-2-pyridylcarbonyl]-L-histidinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)-2-pyridylcarbonyl]-L-histidinate

There total 8 articles about methyl N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)-2-pyridylcarbonyl]-L-histidinate 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:

6-{[Benzyloxycarbonyl-(2-benzyloxycarbonylamino-ethyl)-amino]-methyl}-pyridine-2-carboxylic acid + l-histidine methyl ester dihydrochloride (4467-54-3,5619-10-3,7389-87-9,18684-16-7,22888-60-4,32381-17-2,92742-29-5,100009-20-9) → methyl Nα-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)-2-pyridylcarbonyl]-L-histidinate (209467-29-8)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 75h;

DOI:10.1246/bcsj.71.1159

Reference yield:

methyl 6-formylpicolinate (69950-65-8) → methyl Nα-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)-2-pyridylcarbonyl]-L-histidinate (209467-29-8)

Guidance literature:

Multi-step reaction with 5 steps

1: molecular sieve (4 Angstroem) / acetonitrile / 20 °C

2: NaBH₄ / methanol / 2 h / 20 °C

3: 4.86 g / aq. NaOH / CH₂Cl₂ / 3 h / 20 °C

4: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

5: 615 mg / diphenylphosphoryl azide; Et₃N / dimethylformamide / 75 h / 0 - 20 °C

With lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; diphenylphosphoranyl azide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Reduction / 3: Acylation / 4: Hydrolysis / 5: Condensation;

DOI:10.1246/bcsj.71.1159

Reference yield:

2-benzyloxycarbonylaminoethylamine (72080-83-2) → methyl Nα-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)-2-pyridylcarbonyl]-L-histidinate (209467-29-8)

Guidance literature:

Multi-step reaction with 5 steps

1: molecular sieve (4 Angstroem) / acetonitrile / 20 °C

2: NaBH₄ / methanol / 2 h / 20 °C

3: 4.86 g / aq. NaOH / CH₂Cl₂ / 3 h / 20 °C

4: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

5: 615 mg / diphenylphosphoryl azide; Et₃N / dimethylformamide / 75 h / 0 - 20 °C

With lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; diphenylphosphoranyl azide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Reduction / 3: Acylation / 4: Hydrolysis / 5: Condensation;

DOI:10.1246/bcsj.71.1159

upstream raw materials:

L-histidine methyl ester

methyl 6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)pyridine-2-carboxylate

l-histidine methyl ester dihydrochloride

methyl 6-formylpicolinate

Downstream raw materials:

[2-(Benzyloxycarbonyl-{6-[(S)-1-(2-carbamoyl-ethylcarbamoyl)-2-(3H-imidazol-4-yl)-ethylcarbamoyl]-pyridin-2-ylmethyl}-amino)-ethyl]-carbamic acid benzyl ester

N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-N-[2-(benzyloxycarbonylamino)ethyl]-L-histidinamide

3-{N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-L-histidinylamino}-N-t-butylpropionamide

3-{N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-L-histidinylamino}propionamide

Refernces

• 1、 Arai, Takayuki,Shinozuka, Kazuo,Sawai, Hiroaki. "Bleomycin model complex bearing a carbamoyl derived substituent capable of coordination to the chelated metal ion as a sixth ligand". . p. 15 - 18. Retrieved 2007/10/03.