benzyl (2S,4R)-1-tert-butoxycarbonyl-4-[(4-methylbenzenesulfonyl)oxy]-2-pyrrolidinecarboxylate

Base Information

• Chemical Name: benzyl (2S,4R)-1-tert-butoxycarbonyl-4-[(4-methylbenzenesulfonyl)oxy]-2-pyrrolidinecarboxylate
• CAS No.: 96314-27-1
• Molecular Formula: C₂₄H₂₉NO₇S
• Molecular Weight: 475.563
• Mol file: 96314-27-1.mol

Synonyms:benzyl (2S,4R)-1-tert-butoxycarbonyl-4-[(4-methylbenzenesulfonyl)oxy]-2-pyrrolidinecarboxylate

Chemical Property of benzyl (2S,4R)-1-tert-butoxycarbonyl-4-[(4-methylbenzenesulfonyl)oxy]-2-pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,4R)-1-tert-butoxycarbonyl-4-[(4-methylbenzenesulfonyl)oxy]-2-pyrrolidinecarboxylate

There total 6 articles about benzyl (2S,4R)-1-tert-butoxycarbonyl-4-[(4-methylbenzenesulfonyl)oxy]-2-pyrrolidinecarboxylate 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: 82.0%

N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester (89813-47-8) + p-toluenesulfonyl chloride (98-59-9) → benzyl (2S,4R)-1-tert-butoxycarbonyl-4-[(4-methylbenzenesulfonyl)oxy]-2-pyrrolidinecarboxylate (96314-27-1)

Guidance literature:

With pyridine; In chloroform; at 20 ℃; for 88h;

DOI:10.1016/j.bmc.2007.01.041

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → benzyl (2S,4R)-1-tert-butoxycarbonyl-4-[(4-methylbenzenesulfonyl)oxy]-2-pyrrolidinecarboxylate (96314-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1./KOH 2./Et₃N

2: pyridine

With potassium hydroxide; triethylamine; In pyridine;

DOI:10.1016/S0040-4039(00)83964-7

Reference yield:

benzyl chloride (100-44-7) → benzyl (2S,4R)-1-tert-butoxycarbonyl-4-[(4-methylbenzenesulfonyl)oxy]-2-pyrrolidinecarboxylate (96314-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1./KOH 2./Et₃N

2: pyridine

With potassium hydroxide; triethylamine; In pyridine;

DOI:10.1016/S0040-4039(00)83964-7

upstream raw materials:

N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester

p-toluenesulfonyl chloride

di-tert-butyl dicarbonate

benzyl chloride

Downstream raw materials:

(2S,4R)-1-(tert-butoxycarbonyl)-4-(tosyloxy)pyrrolidine-2-carboxylic acid

benzyl (2S,4S)-1-tert-butoxycarbonyl-4-cyano-2-pyrrolidinecarboxylate

(2S,4S)-2-benzyl 1-tert-butyl 4-((R)-2-amino-3-ethoxy-3-oxopropylsulfanyl)pyrrolidine-1,2-dicarboxylate