132592-07-5

Basic information

• Product Name: （2s，4s）-dibenzyl 4-hydroxypyrrolidine-1，2-dicarboxylate
• Synonyms: （2s，4s）-dibenzyl 4-hydroxypyrrolidine-1，2-dicarboxylate;(2R,4R)-dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate;(2S,4S)-4-hydroxy-1,2-Pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl) ester
• CAS NO: 132592-07-5
• Molecular Formula: C₂₀H₂₁NO₅
• Molecular Weight: 355.388
• Mol File: 132592-07-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 517.884 °C at 760 mmHg
• Flash Point: 267.007 °C
• Appearance: /
• Density: 1.3 g/cm³
• Refractive Index: 1.608
• Storage Temp.: 2-8°C
• CAS DataBase Reference: （2s，4s）-dibenzyl 4-hydroxypyrrolidine-1，2-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: （2s，4s）-dibenzyl 4-hydroxypyrrolidine-1，2-dicarboxylate(132592-07-5)
• EPA Substance Registry System: （2s，4s）-dibenzyl 4-hydroxypyrrolidine-1，2-dicarboxylate(132592-07-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 132592-07-5(Hazardous Substances Data)

Usage

General Description

（2S,4S）-dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate, also known as DBPC, is a chemical compound with a molecular formula C26H27NO5. It is a diastereoisomer of the enantiomer that is used as an anti-epileptic and anti-arrhythmic medication. It is a white crystalline powder that is commonly used as a chiral auxiliary in asymmetric synthesis. DBPC has been found to exhibit anti-inflammatory and analgesic properties, and has also shown potential in the treatment of neurodegenerative diseases. Additionally, it has been found to have antiproliferative and anti-metastatic effects on cancer cells. Due to its potential medicinal properties, DBPC is an active area of research in the pharmaceutical industry.

InChI:InChI=1/C20H21NO5/c22-17-11-18(19(23)25-13-15-7-3-1-4-8-15)21(12-17)20(24)26-14-16-9-5-2-6-10-16/h1-10,17-18,22H,11-14H2/t17-,18-/m0/s1

Upstream product

• 100-39-0 benzyl bromide 
• 197079-48-4 trans-N-(Benzyloxycarbonyl)-4-hydroxy-L-proline 
• 501-53-1 benzyl chloroformate 
• 51-35-4 4-hydroxyproline 
• 618-27-9 hydroxy L-proline 
• 441067-49-8 (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 13500-53-3 N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester 
• 67-56-1 methanol 
• 1015426-34-2 C₂₇H₂₄N₂O₈ 
• 51-35-4 4R-4-hydroxyproline 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 136124-33-9 (4S)-4-hydroxy-L-proline benzyl ester p-toluenesulfonyl salt 

Downstream Products

• 1015426-35-3 C₂₈H₂₄N₂O₇ 
• 836649-32-2 C₂₁H₂₇NO₃Si 
• 1304075-55-5 C₃₆H₃₉NO₅Si 
• 329191-66-4 (2S,4R)-N^α-Cbz-4-aminoproline benzyl ester 
• 1256282-28-6 (2S,4S)-dibenzyl 4-(4-phenylbutanoyloxy)pyrrolidine-1,2-dicarboxylate 
• 1005391-32-1 N^α-benzyloxycarbonyl-trans-4-(4-tert-butylphenoxy)-L-proline benzyl ester 
• 132591-98-1 (2S,4S,5RS)-5-methoxy-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 113949-46-5 (2S,4S)-1-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-4-phenoxy-pyrrolidine-2-carboxylic acid 
• 113949-49-8 (2S,4S)-1-((S)-3-Mercapto-2-methyl-propionyl)-4-phenoxy-pyrrolidine-2-carboxylic acid 
• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 155391-56-3 C₃₀H₃₈N₄O₈S₂ 
• 810685-23-5 (2S,4S)-4-Methoxymethoxy-pyrrolidine-2-carboxylic acid 
• 113949-37-4 cis-4-phenoxy-L-propline 
• 132592-00-8 (2R,4S)-4-Methoxy-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 

Relevant articles and documents

Novel μ opioid antagonists derived from the μ opioid agonists endomorphin and [Dmt1]DALDA (H-Dmt-D-Arg-Phe-Lys-NH2)

Hybrid analogues of the μ opioid agonists endomorphin and [Dmt1]DALDA (H-Dmt-D-Arg-Phe-Lys-NH2, Dmt?=?2′,6′-dimethyltyrosine) containing cis-4-amino-Pro, trans-4-amino-Pro, cis-4-aminoethyl-Pro or cis-4-guanidinylethyl-Pro in the 2 p

Cu(i)-Functionalized SBA-16: An efficient catalyst for the synthesis of α-ketoamides under moderate conditions

An efficient catalyst based on the cage-like mesoporous material SBA-16 as the support and Cu(i) as active sites has been successfully prepared. The catalyst demonstrated high catalytic activity (up to 88%) in the direct oxidative synthesis of α-ketoamides between acetophenone and piperidine, employing O2 from open air as the oxidant without other additives. A heterogeneous catalyst was applied in this reaction for the first time, and the catalyst could be easily separated from the reaction system by filtration and reused several times without a significant loss of activity.

Protected aminooxyprolines for expedited library synthesis: Application to Tsg101-directed proline-oxime containing peptides

The stereoselective synthesis of aminooxy-containing proline analogues bearing Fmoc/Boc or Fmoc/Mtt protection that renders them suitable for incorporation into peptides using Fmoc protocols is reported. Acid-catalyzed unmasking at the completion of peptide synthesis yields free aminooxy-functionalities for oxime formation through reaction with libraries of aldehydes. This allows post solid-phase diversification strategies that may facilitate structure-activity relationship studies.