(2S,4S)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,4S)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester
• CAS No.: 173913-68-3
• Molecular Formula: C₃₅H₃₃NO₃S₂
• Molecular Weight: 579.784
• Mol file: 173913-68-3.mol

Synonyms:(2S,4S)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property of (2S,4S)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester

There total 2 articles about (2S,4S)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester 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:

(2S)-3,3-dimethyl-4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester (173913-63-8) → (2S,4S)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester (173913-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / -78 °C

2: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h, 3.) 4 deg C, overnight

With lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jo9514984

Reference yield:

carbon disulfide (75-15-0,12122-00-8) + (2S,4S)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester (173913-65-0) + methyl iodide (74-88-4) → (2S,4S)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester (173913-68-3)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h, 3.) 4 deg C, overnight;

DOI:10.1021/jo9514984

Reference yield: 81.0%

(2S,4S)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester (173913-68-3) → (2S)-3,3-dimethyl-N-(9-phenylfluoren-9-yl)proline benzyl ester (173913-69-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1021/jo9514984

upstream raw materials:

carbon disulfide

(2S,4S)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester

methyl iodide

(2S)-3,3-dimethyl-4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester

Downstream raw materials:

(2S)-3,3-dimethyl-N-(9-phenylfluoren-9-yl)proline benzyl ester

1-(tert-butoxycarbonyl)-3,3-dimethyl-D,L-proline