benzyl (2S,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsilyloxy-5-oxopyrrolidine-2-carboxylate

Base Information

• Chemical Name: benzyl (2S,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsilyloxy-5-oxopyrrolidine-2-carboxylate
• CAS No.: 1403576-53-3
• Molecular Formula: C₂₃H₃₅NO₆Si
• Molecular Weight: 449.62
• Mol file: 1403576-53-3.mol

Synonyms:benzyl (2S,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsilyloxy-5-oxopyrrolidine-2-carboxylate

Chemical Property of benzyl (2S,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsilyloxy-5-oxopyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsilyloxy-5-oxopyrrolidine-2-carboxylate

There total 2 articles about benzyl (2S,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsilyloxy-5-oxopyrrolidine-2-carboxylate 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: 92.0%

benzyl (2S,4R)-1-tert-butoxycarbonyl-4-hydroxy-5-oxopyrrolidine-2-carboxylate (116857-24-0) + tert-butyldimethylsilyl chloride (18162-48-6) → benzyl (2S,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsilyloxy-5-oxopyrrolidine-2-carboxylate (1403576-53-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 70 ℃; for 3.5h; Inert atmosphere;

DOI:10.3998/ark.5550190.0013.821

Reference yield:

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate (113400-36-5,400626-71-3) → benzyl (2S,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsilyloxy-5-oxopyrrolidine-2-carboxylate (1403576-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

1.2: 0.75 h / -78 °C

1.3: -78 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 3.5 h / 70 °C / Inert atmosphere

With 1H-imidazole; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.3998/ark.5550190.0013.821

upstream raw materials:

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

benzyl (2S,4R)-1-tert-butoxycarbonyl-4-hydroxy-5-oxopyrrolidine-2-carboxylate

tert-butyldimethylsilyl chloride