N-[4-(acetoxy)benzyloxycarbonyl]-glycyl-(S-palmitoyl)-L-cysteyl-L-methionyl-glycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester

Base Information

Chemical Name:N-[4-(acetoxy)benzyloxycarbonyl]-glycyl-(S-palmitoyl)-L-cysteyl-L-methionyl-glycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester
CAS No.:212119-83-0
Molecular Formula:C₆₈H₁₀₉N₇O₁₃S₃
Molecular Weight:1328.85
Hs Code.:

Synonyms:N-[4-(acetoxy)benzyloxycarbonyl]-glycyl-(S-palmitoyl)-L-cysteyl-L-methionyl-glycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester

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Chemical Property of N-[4-(acetoxy)benzyloxycarbonyl]-glycyl-(S-palmitoyl)-L-cysteyl-L-methionyl-glycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester

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Technology Process of N-[4-(acetoxy)benzyloxycarbonyl]-glycyl-(S-palmitoyl)-L-cysteyl-L-methionyl-glycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester

There total 17 articles about N-[4-(acetoxy)benzyloxycarbonyl]-glycyl-(S-palmitoyl)-L-cysteyl-L-methionyl-glycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine 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: 61.0%

: 170892-94-1
L-Methionylglycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester

: (R)-2-[2-(3-Acetoxy-benzyloxycarbonylamino)-acetylamino]-3-hexadecanoylsulfanyl-propionic acid

: 212119-83-0
N-[4-(acetoxy)benzyloxycarbonyl]-glycyl-(S-palmitoyl)-L-cysteyl-L-methionyl-glycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; for 12h; Ambient temperature;
DOI:10.1021/ja9805627

Reference yield:

: 7364-46-7
N-trimethylsilanyl-L-leucine trimethylsilanyl ester

: 212119-83-0
N-[4-(acetoxy)benzyloxycarbonyl]-glycyl-(S-palmitoyl)-L-cysteyl-L-methionyl-glycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 12 h

2: 74 percent / Et₃N, HOBt, DCC / tetrahydrofuran / 0 °C

3: 94 percent / Pd(PPh₃)4, morpholine / tetrahydrofuran / 0.5 h / Ambient temperature

4: 94 percent / HOBt, EDC / CH₂Cl₂ / 24 h / Ambient temperature

5: 65 percent / lipase from Mucor miehei, KI / methanol / 12 h / 37 °C

6: 80 percent / HOBt, EDC / CH₂Cl₂ / 24 h / Ambient temperature

7: 48 percent / lipase from Mucor miehei, KI / methanol / 12 h / 37 °C

8: 61 percent / HOBt, EDC / dimethylformamide / 12 h / Ambient temperature

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lipase from Mucor miehei; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide; potassium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja9805627

Reference yield:

: 63-68-3,26062-47-5,58576-49-1
L-methionine

: 212119-83-0
N-[4-(acetoxy)benzyloxycarbonyl]-glycyl-(S-palmitoyl)-L-cysteyl-L-methionyl-glycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: tetrahydrofuran / 0.5 h / 20 - 50 °C

2: Et₃N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 12 h

3: 62 percent / Et₃N, HOBt, DCC / tetrahydrofuran / 0 °C

4: 95 percent / Pd(PPh₃)4, morpholine / tetrahydrofuran / 0.5 h / Ambient temperature

5: 80 percent / HOBt, EDC / CH₂Cl₂ / 24 h / Ambient temperature

6: 48 percent / lipase from Mucor miehei, KI / methanol / 12 h / 37 °C

7: 61 percent / HOBt, EDC / dimethylformamide / 12 h / Ambient temperature

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lipase from Mucor miehei; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide; potassium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja9805627