N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester
• CAS No.: 210105-90-1
• Molecular Formula: C₅₆H₅₆ClN₃O₁₁
• Molecular Weight: 982.527
• Mol file: 210105-90-1.mol

Synonyms:N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester

Chemical Property of N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester

There total 16 articles about N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester 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: 77.0%

N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosine (57228-57-6) + (S)-2-{[(S)-3-(3-Benzyloxy-2-chloro-4-methoxy-phenyl)-2-methylamino-propionyl]-methyl-amino}-3-phenyl-propionic acid allyl ester (778560-53-5) → N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester (210105-90-1)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3773(19980518)37:9<1236::AID-ANIE1236>3.0.CO;2-F

Reference yield: 77.0%

N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosine (57228-57-6) + (S)-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)phenylalanyl-N-methyl-(S)-phenylalanine allyl ester hydrochloride → N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester (210105-90-1)

Guidance literature:

With hydroxyazobenzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at 0 ℃; for 16h;

DOI:10.1002/(sici)1521-3765(19990104)5:1<227::aid-chem227>3.3.co;2-o

Reference yield:

3-benzyloxy-2-chloro-4-methoxy-benzaldehyde (53713-77-2) → N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester (210105-90-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / NaBH₄ / tetrahydrofuran; methanol / 5 h / 40 °C

2: 85 percent / PPh₃, CBr₄ / diethyl ether / 20 h / Ambient temperature

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 5 h

4: HCl, H₂O / tetrahydrofuran / 16 h / Ambient temperature

5: 88 percent / NEt₃ / methanol / 15 h / Ambient temperature

6: 99 percent / LiOH, H₂O / tetrahydrofuran / 3 h / Ambient temperature

7: 96 percent / NaH / tetrahydrofuran / 16 h / 0 °C

8: 81 percent / hydroxyazobenzotriazole, NEt₃, EDC / dimethylformamide / 1.) 0 deg C, 15 min, 2.) r.t., 14 h

9: HCl / diethyl ether / 1.5 h / Ambient temperature

10: 77 percent / EDC, hydroxyazobenzotriazole, NEt₃ / dimethylformamide / 16 h / 0 °C

With hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; hydroxyazobenzotriazole; water; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1002/(sici)1521-3765(19990104)5:1<227::aid-chem227>3.3.co;2-o

upstream raw materials:

N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosine

(S)-2-{[(S)-3-(3-Benzyloxy-2-chloro-4-methoxy-phenyl)-2-methylamino-propionyl]-methyl-amino}-3-phenyl-propionic acid allyl ester

3-benzyloxy-2-chloro-4-methoxy-benzaldehyde

2-chloro-3-hydroxy-4-methoxybenzaldehyde

Downstream raw materials:

pepticinnamin E

N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine-(R)-(piperazine-2,5-dione)methyl ester

N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine

Refernces

• 1、 Hinterding, Klaus,Hagenbuch, Patrizia,Retey, Janos,Waldmann, Herbert. "Synthesis and in vitro evaluation of the Ras farnesyltransferase inhibitor pepticinnamin E". . p. 1236 - 1239. Retrieved 2007/10/03.