13500-53-3

Usage

Uses

Used in Pharmaceutical Research and Organic Synthesis:
（2s，4r）-1，2-dicarbobenzyloxy-4-hydroxypyrrolidine is utilized as a chiral building block for its ability to form a variety of complex structures, making it instrumental in the development of new pharmaceuticals and organic compounds.
Used in the Synthesis of Pharmaceuticals:
In the pharmaceutical industry, （2s，4r）-1，2-dicarbobenzyloxy-4-hydroxypyrrolidine is used as a key intermediate in the production of biologically active compounds, contributing to the creation of innovative medications.
Used in the Synthesis of Agrochemicals:
Similarly, in agrochemical development, （2s，4r）-1，2-dicarbobenzyloxy-4-hydroxypyrrolidine is employed as a crucial intermediate, facilitating the synthesis of new compounds designed to improve crop protection and yield.
Used in the Production of Fine Chemicals:
（2s，4r）-1，2-dicarbobenzyloxy-4-hydroxypyrrolidine is also used in the synthesis of fine chemicals, where its reactivity and chiral properties are leveraged to produce high-quality specialty chemicals for various applications.

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+/m1/s1

Upstream product

• 100-44-7 benzyl chloride 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 100-51-6 benzyl alcohol 
• 51-35-4 4-hydroxyproline 
• 501-53-1 benzyl chloroformate 
• 100-39-0 benzyl bromide 
• 197079-48-4 trans-N-(Benzyloxycarbonyl)-4-hydroxy-L-proline 
• 2584-71-6 cis-hydroxy-D-proline 
• 51-35-4 4R-4-hydroxyproline 
• 541-41-3 chloroformic acid ethyl ester 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 88501-00-2 (2S,4R)-4-hydroxyproline benzyl ester p-toluenesulfonate 

Downstream Products

• 132592-10-0 (2S,4R)-4-(formyloxy)-1,2-pyrrolidinecarboxylic acid 1,2-bis(phenylmethyl ester) 
• 132592-06-4 (2S,4S)-4-(formyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 132592-11-1 (2S,4R)-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 146900-33-6 (2S,4R)-4-(Benzyloxy-diisopropylamino-phosphanyloxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 132592-09-7 (2S,4R)-4-acetoxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 132591-96-9 (2S,4S)-4-acetoxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 132592-12-2 (2S,4R)-4-methoxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 80134-55-0 N^α-Z-O²-(tetra-O-acetyl-β-D-glucopyranosyl)-Hyp-OBzl 
• 80134-55-0 N^α-Z-O²-(tetra-O-acetyl-β-D-galactopyranosyl)-Hyp-OBzl 
• 132592-07-5 (2S,4S)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 159551-87-8 (2S,4R)-N^α-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester 
• 84969-25-5 4-Keto-1-[(phenylmethoxy)carbonyl]-L-proline benzyl ester 
• 329191-63-1 (2S,4S)-N^α-Cbz-4-bromoproline benzyl ester 

Relevant academic research and scientific papers

Investigation of pH-dependent collagen triple-helix formation

(Figure Presented) Helices on demand: Collagen peptides were engineered to form triple helices under environmental control. The replacement of the hydroxyproline (Hyp) residues in a collagen peptide with carboxylate-modified Hyp residues gave a petide tha

Design and synthesis of fluorinated peptides for analysis of fluorous effects on the interconversion of polyproline helices

The unique interaction between fluorine atoms has been exploited to alter protein structures and to develop synthetic and analytical applications. To expand such fluorous interaction for novel applications, polyproline peptides represent an excellent molecular nanoscaffold for controlling the presentation of perfluoroalkyl groups on their unique secondary structure. We develop approaches to synthesis fluorinated peptides to systematically investigate how the number, location and types of the fluorous groups on polyproline affect the conformation by monitoring the transition between the two major polyproline structures PPI and PPII. This work provides valuable information on how fluorous interaction affects the peptide structure and also benefits the design of functional fluorous molecules.

CYCLIC PEPTIDES AS C5 A RECEPTOR ANTAGONISTS

The invention relates to cyclic peptide derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to cyclic peptide C5a receptor antagonists of formula (Ia)or formula (Ib), or pharmaceutically acceptable salts thereof,wherein R1a, R1b, R2, R3 and R4 areas defined in the description. C5a receptor antagonists are potentially useful in the treatment of a wide range of 1 disorders,including inflammatory disorders and immune disorders.

Structural development of cell-penetrating peptides containing cationic proline derivatives

We designed and synthesized a series of cell-penetrating peptides containing cationic proline derivatives (ProGu) that exhibited responsive changes in their secondary structures to the cellular environment. Effects of the peptide length and steric arrangement of the side chain in cationic proline derivatives [Pro4SGu and Pro4RGu] on their secondary structures and cell membrane permeability were investigated. Moreover, peptides 3 and 8 exhibited efficient intracellular delivery of plasmid DNA.

Scaling the Amphiphilic Character and Antimicrobial Activity of Gramicidin S by Dihydroxylation or Ketal Formation

The acid lability of aliphatic ketals, which often serve as protection groups for 1,2-diols, is influenced by their local structural environment. The acetonide of the protected amino acid cis-dihydroxyproline (Dyp) is a typical protecting group cleavable by traces of TFA. The tricyclic acetonide of the dipeptide d-Hot-Tap is resistant to TFA and thus can serve as a bioorthogonal modification of bioactive peptides. With the aim of improving antimicrobial activity and hemolytic properties, we use these reactivity differences to scale the membrane affinity of the decapeptide Gramicidin S cyclo(d-Phe-Pro-Val-Orn-Leu-)2 (GS). The cis-dihydroxylated amino acids are used to increase the polarity of GS or obversely decrease the polarity by stereoselective ketal formation with an aliphatic ketone. While Dyp (GS mimetic 15) has only minimal influence on the biological properties of GS, d-Hot-Tap at the position of d-Phe1-Pro2 eradicates the biological activity (GS mimetic 16). The acid-stable ketals 17-19 are bioorthogonal modifications which reconstitute the biological activity of GS. We describe an improved synthesis of orthogonally protected Fmoc-Dyp-acetonide (9) and of several Fmoc-d-Hot-Tap-ketals for solid-phase peptide synthesis.

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.

Novel Inhibitors of the Amino Acid Transporters ASCT1 and ASCT2

The invention features compounds and methods relating to novel hydroxy-proline analog inhibitors of the ASCT1 and ASCT2 neutral amino acid transporters. These analogs are potent and selective inhibitors of ASCT2 and ASCT1-mediated amino acid transport as evidenced by significantly reduced glutamine or alanine transport-associated currents or radiolabeled substrate (amino acid) uptake in Xenopus oocytes expressing ASCT2 or ASCT1. Selectivity has been established in the same manner whereby reduced substrate associated current or substrate uptake is unobserved in Xenopus oocytes expressing ATA2, SN1, or EAAT(s) (excitatory amino acid transporter). The compounds and methods of the invention can be used in research or clinical applications (e.g., for the treatment of cancer, microbial infection, or ischemia-related central nervous system injury).

Core-shell silica magnetic microspheres supported proline as a recyclable organocatalyst for the asymmetric aldol reaction

l-4-Hydroxyproline has been successfully grafted onto the core-shell structural silica magnetic microspheres and characterized by elemental analysis, thermo gravimetric analysis (TGA), vibrating sample magnetometry (VSM), high resolution transmission electron microscopy (HRTEM) and Fourier transform infrared (FT-IR). The chiral immobilized catalyst demonstrated high catalytic activity (up to 92%), diastereoselectivity (up to 85:15) and enantioselectivity (up to 80%) in the asymmetric aldol reaction between aldehyde acceptors and ketone donors. On the other hand, the synthesized catalyst could be rapidly separated from the reaction mixture through an external magnetic field and reused up to five runs without any obvious loss of activity, indicating its easy-separated property and excellent recyclability.

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.

Organocatalytic tunable amino acid polymers prepared by controlled radical polymerization

Two families of organocatalytically active polystyrene-based copolymers with tunable incorporations of 4-hydroxyproline have been synthesized using two different controlled radical polymerization technologies: nitroxide-mediated polymerization (NMP) and reversible addition-fragmentation chain transfer (RAFT) polymerization. Both of these methodologies allow ready access to a number of polymeric species with controllable molecular weights, narrow molecular weight distributions (ca. 1.2), and reliable functionality incorporations (between 3 and 26%). The organocatalytic activity and selectivity of the NMP-derived family of copolymers with variable incorporations of l-proline have been investigated using the aldol reaction, which provided high conversion to products (>95%) with very good diastereo- and enantioselectivities. We propose that these materials have potential as highly efficient recoverable organocatalyst supports whose solubility and loading can be readily tailored to the desired application.