N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester
• CAS No.: 145763-39-9
• Molecular Formula: C₄₄H₄₉N₅O₁₁S
• Molecular Weight: 855.966
• Mol file: 145763-39-9.mol

Synonyms:N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester

Chemical Property of N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester

There total 7 articles about N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl 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: 58.0%

glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester (68709-94-4) + N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosine (145763-43-5) → N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester (145763-39-9)

Guidance literature:

With 4-methyl-morpholine; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; 1.) 0 deg C, 2 h, 2.) 25 deg C, 16 h;

DOI:10.1016/S0957-4166(00)82083-2

Reference yield:

N-benzyloxycarbonyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester (68835-85-8) → N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester (145763-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / H₂ / 10percent Pd/C / methanol / 760 Torr

2: 58 percent / N-methyl morpholine, N,N-dicyclohexylcarbodiimide (DCC) / CH₂Cl₂; dimethylformamide / 1.) 0 deg C, 2 h, 2.) 25 deg C, 16 h

With 4-methyl-morpholine; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(00)82083-2

Reference yield:

4-tosyloxybenzaldehyde (80459-48-9) → N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester (145763-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) potassium t-butoxide / 1.) CH₂Cl₂, -60 deg C, 10 min, 2.) CH₂Cl₂, from -60 deg C to RT, 3 h

2: 75 percent / 1 N aq. NaOH / acetone / 3 h / Ambient temperature

3: 58 percent / N-methyl morpholine, N,N-dicyclohexylcarbodiimide (DCC) / CH₂Cl₂; dimethylformamide / 1.) 0 deg C, 2 h, 2.) 25 deg C, 16 h

With 4-methyl-morpholine; sodium hydroxide; potassium tert-butylate; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0957-4166(00)82083-2

upstream raw materials:

glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester

N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosine

4-tosyloxybenzaldehyde

2-Benzyloxycarbonylamino-2-diethyloxyphosphoryl-essigsaeure-ethylester

Downstream raw materials:

(S)-2-{(S)-2-[2-(2-{2-Benzyloxycarbonylamino-3-[4-(toluene-4-sulfonyloxy)-phenyl]-propionylamino}-acetylamino)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester