[4-(5-{4-[(2S,4R)-2-(Bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentyloxy)-5-methoxy-2-nitro-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone

Base Information

• Chemical Name: [4-(5-{4-[(2S,4R)-2-(Bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentyloxy)-5-methoxy-2-nitro-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone
• CAS No.: 929049-13-8
• Molecular Formula: C₃₉H₅₄F₂N₄O₁₀S₄
• Molecular Weight: 905.139
• Mol file: 929049-13-8.mol

Synonyms:

Chemical Property of [4-(5-{4-[(2S,4R)-2-(Bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentyloxy)-5-methoxy-2-nitro-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [4-(5-{4-[(2S,4R)-2-(Bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentyloxy)-5-methoxy-2-nitro-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone

There total 5 articles about [4-(5-{4-[(2S,4R)-2-(Bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentyloxy)-5-methoxy-2-nitro-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone 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:

(2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (929049-03-6) → [4-(5-{4-[(2S,4R)-2-(Bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentyloxy)-5-methoxy-2-nitro-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone (929049-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / TMSCl / CHCl₃ / 24 h / 20 °C

2: 80 percent / EtSH*BF₃OEt₂ / CH₂Cl₂ / 12 h / 20 °C

3: K₂CO₃ / acetone / Heating

With chloro-trimethyl-silane; EtSH*BF₃OEt₂; potassium carbonate; In dichloromethane; chloroform; acetone;

DOI:10.1016/j.bmcl.2006.10.070

Reference yield:

methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxylate (929049-02-5) → [4-(5-{4-[(2S,4R)-2-(Bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentyloxy)-5-methoxy-2-nitro-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone (929049-13-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / DIBAL-H / CH₂Cl₂ / 0.75 h / -78 °C

2: 85 percent / TMSCl / CHCl₃ / 24 h / 20 °C

3: 80 percent / EtSH*BF₃OEt₂ / CH₂Cl₂ / 12 h / 20 °C

4: K₂CO₃ / acetone / Heating

With chloro-trimethyl-silane; EtSH*BF₃OEt₂; diisobutylaluminium hydride; potassium carbonate; In dichloromethane; chloroform; acetone;

DOI:10.1016/j.bmcl.2006.10.070

Reference yield:

methyl-(2S,4S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-hydroxypyrrolidine-2-carboxylate → [4-(5-{4-[(2S,4R)-2-(Bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentyloxy)-5-methoxy-2-nitro-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone (929049-13-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / DAST / CH₂Cl₂ / 12 h / -78 - 20 °C

2: 80 percent / DIBAL-H / CH₂Cl₂ / 0.75 h / -78 °C

3: 85 percent / TMSCl / CHCl₃ / 24 h / 20 °C

4: 80 percent / EtSH*BF₃OEt₂ / CH₂Cl₂ / 12 h / 20 °C

5: K₂CO₃ / acetone / Heating

With chloro-trimethyl-silane; EtSH*BF₃OEt₂; diisobutylaluminium hydride; potassium carbonate; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; chloroform; acetone;

DOI:10.1016/j.bmcl.2006.10.070

upstream raw materials:

(2S,4R)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]-4-fluoropyrrolidine-2-carboxaldehyde diethyl-dithioacetal

1,5-dibromo-pentane

(2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde

methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxylate

Downstream raw materials:

[2-Amino-4-(5-{5-amino-4-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentyloxy)-5-methoxy-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone