4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine

Base Information

• Chemical Name: 4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine
• CAS No.: 244089-24-5
• Molecular Formula: C₄₀H₄₇N₅O₇
• Molecular Weight: 709.842
• Mol file: 244089-24-5.mol

Synonyms:4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine

Chemical Property of 4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine

There total 9 articles about 4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine 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: 76.0%

4?benzyloxy?2,6?diaminopyridine (18986-54-4) + 1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-phenylethyl)carbamate (133010-06-7) → 4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine (244089-24-5)

Guidance literature:

4?benzyloxy?2,6?diaminopyridine; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 20 ℃; for 2h;

1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-phenylethyl)carbamate; With tetrabutyl ammonium fluoride; In acetonitrile; at 20 ℃; for 12h; Further stages.;

DOI:10.1002/1521-3765(20010504)7:9<1889::AID-CHEM1889>3.0.CO;2-7

Reference yield:

4?benzyloxy?2,6?diaminopyridine (18986-54-4) → 4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine (244089-24-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 91 percent / 4-DMAP / CH₂Cl₂ / 24 h / 20 °C

2.1: 99 percent / H₂ / 10percent Pd/C / ethanol; CH₂Cl₂ / 18 h / 20 °C

3.1: 99 percent / K₂CO₃; TBAB / dimethylsulfoxide / 18 h / 20 °C

4.1: aq. TFA / CH₂Cl₂

5.1: N,O-bis(trimethylsilylacetamide) / acetonitrile / 2 h / 20 °C

5.2: TBAF / acetonitrile / 12 h / 20 °C

With dmap; N,O-bis-(trimethylsilyl)-acetamide; tetrabutylammomium bromide; hydrogen; potassium carbonate; trifluoroacetic acid; 10percent Pd/C; In ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/1521-3765(20010504)7:9<1889::AID-CHEM1889>3.0.CO;2-7

Reference yield:

di-tert-butyl(4-(benzyloxy)pyridine-2,6-diyl)bis(tert-butoxycarbonylcarbamate) (350697-61-9) → 4-Benzyloxy-2,6-bis(N-tert-butoxycarbonyl-L-phenylalaninylamino)pyridine (244089-24-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / H₂ / 10percent Pd/C / ethanol; CH₂Cl₂ / 18 h / 20 °C

2.1: 99 percent / K₂CO₃; TBAB / dimethylsulfoxide / 18 h / 20 °C

3.1: aq. TFA / CH₂Cl₂

4.1: N,O-bis(trimethylsilylacetamide) / acetonitrile / 2 h / 20 °C

4.2: TBAF / acetonitrile / 12 h / 20 °C

With N,O-bis-(trimethylsilyl)-acetamide; tetrabutylammomium bromide; hydrogen; potassium carbonate; trifluoroacetic acid; 10percent Pd/C; In ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/1521-3765(20010504)7:9<1889::AID-CHEM1889>3.0.CO;2-7

upstream raw materials:

1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-phenylethyl)carbamate

4?benzyloxy?2,6?diaminopyridine

(2,6-diamino-pyridin-4-yloxy)-acetic acid benzyl ester

dibenzyl 4-(benzyloxy)-2,6-pyridinedicarboxylate

Downstream raw materials:

Benzyl 2-{[2,6-bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyl]oxy} acetate

2-{2,6-Bis[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-4-pyridyloxy} acetic acid

{2,6-bis-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-pyridin-4-yloxy}-acetic acid benzyl ester

2-[2,6-Bis(N-tert-butoxycarbonyl-L-phenylalanylamino)-4-pyridyloxy] acetic acid