methyl N-(p-nitrobenzenesulfonyl)-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate

Base Information

• Chemical Name: methyl N-(p-nitrobenzenesulfonyl)-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate
• CAS No.: 312311-70-9
• Molecular Formula: C₃₀H₃₃N₃O₇S
• Molecular Weight: 579.674
• Mol file: 312311-70-9.mol

Synonyms:methyl N-(p-nitrobenzenesulfonyl)-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate

Chemical Property of methyl N-(p-nitrobenzenesulfonyl)-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl N-(p-nitrobenzenesulfonyl)-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate

There total 12 articles about methyl N-(p-nitrobenzenesulfonyl)-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate 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:

methyl (S)-3-allylamino-4-phenylbutanoate (312311-69-6) + (S)-3-(4-Nitro-benzenesulfonylamino)-4-phenyl-butyryl chloride → methyl N-(p-nitrobenzenesulfonyl)-(S)-β3-homophenylalanyl-N-allyl-(S)-β3-homophenylalaninate (312311-70-9)

Guidance literature:

With pyridine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(00)00666-9

Reference yield:

L-Phenylalaninol (3182-95-4) → methyl N-(p-nitrobenzenesulfonyl)-(S)-β3-homophenylalanyl-N-allyl-(S)-β3-homophenylalaninate (312311-70-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / CH₂Cl₂ / 10 h / 20 °C

1.2: 95 percent / KOH / H₂O

2.1: H₂O; acetonitrile / 16 h / 20 °C

3.1: 40.98 g / H₂O; HCl / acetic acid / 4 h / Heating

4.1: 90 percent / PTSA / 20 h / Heating

5.1: K₂CO₃ / dimethylformamide; H₂O / 18 h / 20 °C

6.1: 2.15 g / mercaptoacetic acid; DBU / dimethylformamide; H₂O / 3 h

7.1: 4.26 g / pyridine / tetrahydrofuran / 2 h / 20 °C

With pyridine; hydrogenchloride; water; potassium carbonate; toluene-4-sulfonic acid; mercaptoacetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 1.2: Cyclization / 2.1: Addition / 3.1: Hydrolysis / 4.1: Esterification / 5.1: Alkylation / 6.1: Substitution / 7.1: Acylation;

DOI:10.1016/S0040-4020(00)00666-9

Reference yield:

(S)-N-(p-nitrobenzenesulfonyl)-2-benzylaziridine (219738-95-1) → methyl N-(p-nitrobenzenesulfonyl)-(S)-β3-homophenylalanyl-N-allyl-(S)-β3-homophenylalaninate (312311-70-9)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂O; acetonitrile / 16 h / 20 °C

2: 40.98 g / H₂O; HCl / acetic acid / 4 h / Heating

3: 90 percent / PTSA / 20 h / Heating

4: K₂CO₃ / dimethylformamide; H₂O / 18 h / 20 °C

5: 2.15 g / mercaptoacetic acid; DBU / dimethylformamide; H₂O / 3 h

6: 4.26 g / pyridine / tetrahydrofuran / 2 h / 20 °C

With pyridine; hydrogenchloride; water; potassium carbonate; toluene-4-sulfonic acid; mercaptoacetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1: Addition / 2: Hydrolysis / 3: Esterification / 4: Alkylation / 5: Substitution / 6: Acylation;

DOI:10.1016/S0040-4020(00)00666-9

upstream raw materials:

methyl (S)-3-allylamino-4-phenylbutanoate

L-Phenylalaninol

methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-phenylbutanoate

(S)-3-<(tert-butoxycarbonyl)amino>-4-phenylbutanenitrile

Downstream raw materials:

H-β³-hPhe-N-allyl-β³-hPhe-OMe

Ns-β³-hPhe-N-allyl-β³-hPhe-OH

Ns-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-OMe

cyclo(N-(2-azidoethyl)-β³-hPhe-β³-hPhe-N-(2-azidoethyl)-β³-hPhe-β³-hPhe)