182556-78-1

Basic information

• Product Name: (2S,3S)-3-Benzoyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
• CAS NO: 182556-78-1
• Molecular Weight: 335.357
• Mol File: 182556-78-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S)-3-Benzoyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-Benzoyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester(182556-78-1)
• EPA Substance Registry System: (2S,3S)-3-Benzoyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester(182556-78-1)

Safety Data

• Hazardous Substances Data: 182556-78-1(Hazardous Substances Data)

Upstream product

• 166383-70-6 (2R,3S)-1-t-Butoxycarbonyl-3-benzoyloxy-2-benzyloxymethylpyrrolidine 
• 166383-69-3 (2R,3R)-1-t-Butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine 
• 65-85-0 benzoic acid 

Downstream Products

• 166383-71-7 (3S)-1-t-butoxycarbonyl-3-benzoyloxy-N-t-butyl-L-prolinamide 

Relevant articles and documents

Structure-activity relationships of HIV-1 PR inhibitors containing AHPBA - II. Modification of pyrrolidine ring at P1' proline

Systematic replacement in the 3- or 4-position of the pyrrolidine ring at P1' proline was carried out. Compound 26, which has a Cl atom in the 4(S)-position was the most active among inhibitors substituted with other halogen atoms or other substituents. Furthermore, the replacement of the Z group in compound 26 with five- or six-membered fused aromatic heterocycle carbonyl groups produced more potent inhibitors. 7-Methoxybenzofuran-2-carbonyl derivative (44) was the best of these and showed K(i) = 4.5 nM against HIV PR and IC90s 0.58 μM and 0.06 μM in chronic and acute infections, respectively. These results suggest that the combination of the 4(S)-Cl atom and fused bicyclic heterocycles may be effective in improving their cellular penetration.