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

Base Information

• Chemical Name: (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal
• CAS No.: 717920-69-9
• Molecular Formula: C₂₄H₂₉FN₂O₅S₂
• Molecular Weight: 508.635
• Mol file: 717920-69-9.mol

Synonyms:(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal

Chemical Property of (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal

There total 3 articles about (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal 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: 90.0%

ethanethiol (75-08-1) + (2S,4S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (717920-68-8) → (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal (717920-69-9)

Guidance literature:

With chloro-trimethyl-silane; In chloroform; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2004.02.063

Reference yield:

methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate (382137-65-7) → (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal (717920-69-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / DAST / CH₂Cl₂ / 12 h / -78 - 20 °C

2: 85 percent / DIBAL-H / CH₂Cl₂ / 0.75 h / -78 °C

3: 90 percent / TMSCl / CHCl₃ / 24 h / 20 °C

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

DOI:10.1016/j.bmcl.2004.02.063

Reference yield:

methyl (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxylate (717920-67-7) → (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal (717920-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / DIBAL-H / CH₂Cl₂ / 0.75 h / -78 °C

2: 90 percent / TMSCl / CHCl₃ / 24 h / 20 °C

With chloro-trimethyl-silane; diisobutylaluminium hydride; In dichloromethane; chloroform;

DOI:10.1016/j.bmcl.2004.02.063

upstream raw materials:

ethanethiol

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

methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate

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

Downstream raw materials:

1,1'-{[(pentane-1,5-diyl)dioxy]bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoropyrrolidine-2-carboxaldehyde diethylthioacetal]

1,1'-{[(butane-1,4-diyl)dioxy]bis[(2-nitro-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoropyrrolidine-2-carboxaldehyde diethylthioacetal]

1,1'-{[(butane-1,4-diyl)dioxy]bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoropyrrolidine-2-carboxaldehyde diethylthioacetal]

1,1'-{[(propane-1,3-diyl)dioxy]bis[(2-nitro-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoropyrrolidine-2-carboxaldehyde diethylthioacetal]