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

Base Information

• Chemical Name: (2S,4R)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]-4-fluoropyrrolidine-2-carboxaldehyde diethyl-dithioacetal
• CAS No.: 929049-05-8
• Molecular Formula: C₁₇H₂₃FN₂O₅S₂
• Molecular Weight: 418.51
• Mol file: 929049-05-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (2S,4R)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]-4-fluoropyrrolidine-2-carboxaldehyde diethyl-dithioacetal 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%

(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal (929049-04-7) → (2S,4R)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]-4-fluoropyrrolidine-2-carboxaldehyde diethyl-dithioacetal (929049-05-8)

Guidance literature:

With EtSH*BF₃OEt₂; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2006.10.070

Reference yield:

(2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (929049-03-6) → (2S,4R)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]-4-fluoropyrrolidine-2-carboxaldehyde diethyl-dithioacetal (929049-05-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1016/j.bmcl.2006.10.070

Reference yield:

methyl-(2S,4S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-hydroxypyrrolidine-2-carboxylate → (2S,4R)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]-4-fluoropyrrolidine-2-carboxaldehyde diethyl-dithioacetal (929049-05-8)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1016/j.bmcl.2006.10.070

upstream raw materials:

(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal

(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-(3-{5-amino-4-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-propoxy)-5-methoxy-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone

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

[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

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