130830-77-2

Usage

Derivative of pyrrolidine

This indicates that the compound is derived from pyrrolidine, a chemical structure that is the basis for many pharmaceuticals and agrochemicals.

Building block in the synthesis of various pharmaceuticals and agrochemicals

This indicates that the compound is commonly used as an intermediate in the synthesis of other chemicals, particularly in the pharmaceutical and agrochemical industries.

White solid

This describes the physical appearance of the compound, which is a white solid.

Melting point

260-262 °C This is the temperature range at which the compound changes from a solid to a liquid state.

Chiral molecule

This indicates that the compound has a specific three-dimensional structure that is not superimposable on its mirror image, which can have important implications for its chemical properties and biological activity.

(2R,4S) configuration

This specifies the particular arrangement of the atoms in the compound, which is the more commonly encountered form.

Not known to have significant toxicological effects

This indicates that the compound is not known to have harmful effects on human health or the environment.

Relatively safe for commercial and industrial use

This indicates that the compound is considered to be safe for use in commercial and industrial applications, based on current knowledge and regulations.

Upstream product

• 130830-63-6 N-(benzyloxycarbonyl)-cis-4-(tosyloxy)-D-proline ethyl ester 
• 135999-85-8 tetraethyl 1-acetamido-4-hydroxybutane-1,1,3,3-tetracarboxylate 
• 6671-85-8 2-azabicyclo[2.2.1]hept-5-ene 
• 130830-67-0 N-(benzyloxycarbonyl)-trans-4-cyano-D-proline ethyl ester 
• 130930-27-7 (2R,4R)-2-ethoxycarbonyl-4-hydroxy-N-(benzyloxycarbonyl)pyrrolidine 
• 130830-75-0 N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline 
• 135999-86-9 2-Acetylamino-2,4-bis-ethoxycarbonyl-4-(toluene-4-sulfonyloxymethyl)-pentanedioic acid diethyl ester 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 2584-71-6 cis-hydroxy-D-proline 
• 130830-71-6 N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester 
• 139927-14-3 (+/-)-2-benzoyl-2-azabicyclo<2.2.1>hept-5-ene 
• 130930-25-5 (R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 188345-72-4 2,2,2-trichloroethyl (+/-)-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 188345-71-3 2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]hept-5-ene 

Relevant academic research and scientific papers

Stereospecific synthesis of cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5-piperidinedicarboxylic acid

Lactams derived from hetero Diels-Alder adducts were stereospecifically converted into cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5- piperidinedicarboxylic acid by ruthenium tetroxide oxidation. Optically active (2S,4S)-(-)-2,4-pyrrolidinedicarboxylic acid and (2R,4R)-(+)-2,4- pyrrolidinedicarboxylic acid were synthesized from (1S,4R)-(+)-2- azabicyclo[2.2.1]hept-5-en-3-one and (1R,4S)-(-)-2-azabicyclo[2.2.1]hept-5- en-3-one, respectively.

An enantioselective route to pyrrolidines: Removal of the chiral template from homochiral pyrroloimidazoles

Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral imidazolinium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g. naturally occurring proline derivatives and homochiral pyrrolizidines.

Synthesis of two cyclic analogs of glutamic acid: cis- and trans-pyrrolidine-2,4-dicarboxylic acids

The tosyl ester 2 of tetraethyl 1-acetamido-4-hydroxybutane- 1,1,3,3-tetracarboxylate gave 4-methylene glutammic acid in 90% yield by refluxing with concentrated HC1. Treatment of 2 with NaOEt, then with refluxing concentrated HC1 gave a 54% yield of cis

Conformationally Defined Neurotransmitter Analogues. Selective Inhibition of Glutamate Uptake by One Pyrrolidine-2,4-dicarboxylate Diastereomer

In order to determine the conformational requirements for binding of L-glutamate to the proteins involved in the process of neurotransmission, rigid analogues containing an embedded glutamate moiety have been prepared.These "conformer mimics", the pyrrolidine-2,4-dicarboxylates 4, 7, 11, and 14, were synthesized from commercially available trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline, and then were tested for their ability to inhibit the high-affinity transport of -L-glutamate into synaptosomes and to block the binding of radioligands to the NMDA (N-methyl-D-aspartate), KA (kainate), and QA (quisqualate) glutamate neurotransmitter receptor sites.While none of the four analogues binds effectively to the excitatory receptors, the L-trans-isomer 7 is a potent and selective competitive inhibitor of L-glutamate transport.These results delineate a specific structural/conformational preference for binding to the uptake system that is distinct from that required for binding to the NMDA, KA, and QA receptors.