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

Base Information

• Chemical Name: 1,1'-{[(propane-1,3-diyl)dioxy]bis[(2-nitro-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoropyrrolidine-2-carboxaldehyde diethylthioacetal]
• CAS No.: 717920-73-5
• Molecular Formula: C₃₇H₅₀F₂N₄O₁₀S₄
• Molecular Weight: 877.086
• Mol file: 717920-73-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

1,3-dibromo-propane (109-64-8) + (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal (717920-70-2) → 1,1'-{[(propane-1,3-diyl)dioxy]bis[(2-nitro-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoropyrrolidine-2-carboxaldehyde diethylthioacetal] (717920-73-5)

Guidance literature:

With potassium carbonate; In acetone; Heating;

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) → 1,1'-{[(propane-1,3-diyl)dioxy]bis[(2-nitro-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoropyrrolidine-2-carboxaldehyde diethylthioacetal] (717920-73-5)

Guidance literature:

Multi-step reaction with 5 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

4: 75 percent / EtSH; BF₃*OEt₂ / CH₂Cl₂ / 12 h / 20 °C

5: K₂CO₃ / acetone / Heating

With chloro-trimethyl-silane; boron trifluoride diethyl etherate; diisobutylaluminium hydride; potassium carbonate; 4,4'-diaminostilbene-2,2'-disulfonic acid; ethanethiol; In dichloromethane; chloroform; acetone;

DOI:10.1016/j.bmcl.2004.02.063

Reference yield:

(2S,4S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (717920-68-8) → 1,1'-{[(propane-1,3-diyl)dioxy]bis[(2-nitro-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoropyrrolidine-2-carboxaldehyde diethylthioacetal] (717920-73-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / TMSCl / CHCl₃ / 24 h / 20 °C

2: 75 percent / EtSH; BF₃*OEt₂ / CH₂Cl₂ / 12 h / 20 °C

3: K₂CO₃ / acetone / Heating

With chloro-trimethyl-silane; boron trifluoride diethyl etherate; potassium carbonate; ethanethiol; In dichloromethane; chloroform; acetone;

DOI:10.1016/j.bmcl.2004.02.063

upstream raw materials:

1,3-dibromo-propane

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

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

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

Downstream raw materials:

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