69669-21-2

Usage

Chemical compound

2,5-Pyrrolidinedione,3,4-dihydroxy-1-phenyl-, (3R,4R)-

Also known as

(R,R)-Tartaric acid amide

Chiral molecule

It has two non-superimposable mirror image forms

Uses

Chiral resolving agent in organic synthesis
Resolving agent for amino acid derivatives
Resolving agent in the pharmaceutical industry for separation of racemic mixtures
Potential applications in the development of catalysts and production of biologically active compounds

Upstream product

• 87-69-4 L-Tartaric acid 
• 62-53-3 aniline 

Downstream Products

• 209625-75-2 (3S,4S)-1-phenylpyrrolidine-3,4-diol 
• 1315329-82-8 C₁₇H₁₂ClNO₅ 
• 1315329-76-0 (3R,4R)-N-phenyl-3,4-bis(2-chlorobenzoyloxy)pyrrolidine-2,5-dione 
• 1315329-67-9 (3R,4R)-N-phenyl-4-benzoyloxy-3-hydroxypyrrolidine-2,5-dione 
• 1315329-83-9 C₁₇H₁₂FNO₅ 
• 1315329-85-1 C₂₄H₁₅F₂NO₆ 
• 880497-74-5 (3R,4R)-3,4-diamino-1-phenylpyrrolidine 
• 1428558-83-1 (3R,4R)-N₃,N₄-bis[3,5-di-t-butylsalicylidene]-1-phenyl-3,4-diaminopyrrolidine 
• 1428558-85-3 C₃₂H₂₇N₃O₂ 
• 209625-79-6 (3R,4R)-3,4-diacetoxy-1-phenylpyrrolidine-2,5-dione 
• 1319721-79-3 C₄NH₂(O)2(C₆H₅)(OC(O)C₅NH₄)2 

Relevant academic research and scientific papers

Synthesis of 3,4-dihydroxypyrrolidine-2,5-dione and 3,5-dihydroxybenzoic acid derivatives and evaluation of the carbonic anhydrase I and II inhibition

The inhibition of two human cytosolic carbonic anhydrase (hCA, EC 4.2.1.1) isozymes I and II, with some 3,4-dihydroxypyrrolidine-2,5-dione and 3,5-dihydroxybenzoic acid derivatives, were investigated by using the esterase assay, with 4-nitrophenyl acetate (4-NPA) as substrate. Compounds 10-13 showed KI values in the range of 112.7-441.5 μM for hCA I and of 3.5-10.76 μM against hCA II, respectively. These hydroxyl group containing compounds generally were competitive inhibitors. Some hydroxyl group containing compounds investigated here showed effective hCA II inhibitory effects, in the same range as the clinically used sulfonamide acetazolamide, and might be used as leads for generating enzyme inhibitors possibly targeting other CA isoforms which have not been yet assayed for their interactions with such agents.

The synthesis of tetradentate salens derived from (3R,4R)-N-substituted-3, 4-diaminopyrrolidines and their application in the enantioselective trimethylsilylcyanation of aromatic aldehydes

The in situ formed Ti(IV) complexes of pyrrolidine-based chiral salen ligands derived from natural l-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of aromatic aldehydes. The different activity and selectivity of the catalysts in the formation of the products were found to be dependent on the N-substituent of the pyrrolidine.