(R)-2-{[(S)-1-((S)-2-{2-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester

Base Information

• Chemical Name: (R)-2-{[(S)-1-((S)-2-{2-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester
• CAS No.: 170892-93-0
• Molecular Formula: C₄₇H₇₁N₅O₁₀S₂
• Molecular Weight: 930.24

Synonyms:(R)-2-{[(S)-1-((S)-2-{2-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester

Chemical Property of (R)-2-{[(S)-1-((S)-2-{2-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester

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Technology Process of (R)-2-{[(S)-1-((S)-2-{2-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester

There total 15 articles about (R)-2-{[(S)-1-((S)-2-{2-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid 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: 80.0%

[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetic acid (170892-92-9) + L-Leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester (170892-91-8) → (R)-2-{[(S)-1-((S)-2-{2-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester (170892-93-0)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide;

Reference yield:

(S)-1-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid (170892-89-4) → (R)-2-{[(S)-1-((S)-2-{2-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester (170892-93-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / HOBt, EDC / CH₂Cl₂ / 24 h / Ambient temperature

2: 65 percent / lipase from Mucor miehei, KI / methanol / 12 h / 37 °C

3: 80 percent / HOBt, EDC / CH₂Cl₂ / 24 h / Ambient temperature

With lipase from Mucor miehei; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; potassium iodide; In methanol; dichloromethane;

DOI:10.1021/ja9805627

Reference yield:

(R)-2-({(S)-1-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carbonyl}-amino)-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester (170892-90-7) → (R)-2-{[(S)-1-((S)-2-{2-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester (170892-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / lipase from Mucor miehei, KI / methanol / 12 h / 37 °C

2: 80 percent / HOBt, EDC / CH₂Cl₂ / 24 h / Ambient temperature

With lipase from Mucor miehei; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; potassium iodide; In methanol; dichloromethane;

DOI:10.1021/ja9805627

upstream raw materials:

[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methylsulfanyl-butyrylamino]-acetic acid

L-Leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester

N-trimethylsilanyl-L-leucine trimethylsilanyl ester

L-leucine

Downstream raw materials:

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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