132592-07-5

Usage

Uses

Used in Pharmaceutical Industry:
DBPC is utilized as a chiral auxiliary in asymmetric synthesis for the development of enantiomerically pure compounds, which is crucial for ensuring the desired biological activity and safety of pharmaceuticals.
Used in Anti-inflammatory and Analgesic Applications:
DBPC is employed as an anti-inflammatory and analgesic agent, leveraging its ability to reduce inflammation and alleviate pain, which can be beneficial in the treatment of various conditions characterized by inflammation and pain.
Used in Neurodegenerative Disease Treatment:
DBPC is used as a potential treatment for neurodegenerative diseases due to its neuroprotective properties, which may help slow down or halt the progression of these debilitating conditions.
Used in Anticancer Applications:
DBPC is used as an anticancer agent, exhibiting antiproliferative and anti-metastatic effects on cancer cells, which can contribute to the development of novel therapeutic strategies against cancer.
Used in Drug Development Research:
DBPC is used in research for drug development, particularly in the exploration of its potential medicinal properties and the discovery of new therapeutic agents with improved efficacy and safety profiles.

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

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

Downstream Products

• 132591-97-0 (2S,4S)-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 113949-37-4 cis-4-phenoxy-L-propline 
• 1015426-35-3 C₂₈H₂₄N₂O₇ 
• 836649-32-2 C₂₁H₂₇NO₃Si 
• 1304075-55-5 C₃₆H₃₉NO₅Si 
• 329191-66-4 (2S,4R)-N^α-Cbz-4-aminoproline benzyl ester 
• 77884-93-6 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-L-arabinopyranosyl)-L-hydroxyproline 
• 77884-93-6 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-arabinopyranosyl)-L-hydroxyproline 
• 77871-03-5 2-N-(benzyloxycarbonyl)-4-O-(2,3,5-tri-O-benzyl-α-L-arabinofuranosyl)-L-hydroxyproline benzyl ester 
• 77871-03-5 2-N-(benzyloxycarbonyl)-4-O-(2,3,5-tri-O-benzyl-β-L-arabinofuranosyl)-L-hydroxyproline benzyl ester 
• 77871-03-5 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-arabinofuranosyl)-L-hydroxyproline 
• 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) 

Relevant academic research and scientific papers

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

DIMERIC PEPTIDE INHIBITORS OF APOPTOSIS PROTEINS

The present technology is directed to compounds, compositions, and methods related to treatment of cancers and viral infections mediated by lAPs. In particular the present compounds and compositions may be used to treat lAP-mediated ovarian cancer and hepatitis B infection.

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.

L-proline-catalyzed asymmetric michael addition of 2-oxindoles to enones: A convenient access to oxindoles with a quaternary stereocenter

A new organocatalytic approach for 1,4-conjugate addition of 2-oxindoles to α,β-unsaturated ketones using the combination of readily available and nonexpensive l-proline and achiral trans-2,5-dimethylpiperazine as catalytic system is provided. The reaction results in oxindole derivatives with vicinal quaternary and tertiary carbon centers in up to 99% yield and 91% ee. Georg Thieme Verlag Stuttgart.

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.

Highly efficient asymmetric direct stoichiometric aldol reactions on/in water

(Figure Presented) Hydrophobic pocket pleaser: A novel asymmetric catalytic system in water mediated by sulfated β-cyclodextrin (see picture) can bind the organocatalyst tert-butylphenoxyproline and associated hydrophobic reactants. Enantio- and diastereoselectivities up to >99% and close to quantitative yields could be achieved for stoichiometric direct aldol reactions of cyclohexanone and aryl aldehydes with this system.

Catalysis with phosphine-containing amino acids in various "turn" motifs

We have been actively involved in the development of parallel approaches for the discovery of phosphine ligands. Our approach has been based on the incorporation of phosphine-containing amino acids into peptide sequences that are designed to have stable secondary structures. We have examined helical and turn secondary structures and have reported that alkylation of cyclopentenyl acetate with dimethylmalonate can be catalyzed in high enantiomeric excess (ee) with a β-turn-based ligand. The importance of the peptide secondary structure was demonstrated through the synthesis of a series of peptide ligands where the nature of the turn-forming residues was probed. Additionally, other turn-forming units and a variety of different phosphine-containing amino acids have been examined for their ability to control the selectivity of the allylation reaction. This paper reports the results obtained through the examination of different turn motifs as well as different phosphine substitutions on the "best" turn sequence, Pps-Pro-D-Xxx-Pps.

Synthesis of De(hydroxymethyl)desulfo Analogues of Bulgecins A, B and C

The syntheses of de(hydroxymethyl)desulfo analogues of Bulgecin A, B and C are described.Stereospecific β-glycosylation of aglycones was achieved using Schmidt's trichloroacetimidate metodology.

Electrochemical Oxidation of Proline Derivatives: Total Syntheses of Bulgecinine and Bulgecin C

The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented.Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) ester (19).The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent.Bulgecin C (1c) was prepared via a β-stereoselective glycosidation reaction using a 2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.