64191-14-6

Usage

Uses

Used in Laboratory Research:
(1S,2R)-2-Aminocyclopentanecarboxylic acid is used as a building block in organic chemistry for the synthesis of peptides, contributing to the development of novel compounds with specific properties and functions.
Used in Medicinal Chemistry:
(1S,2R)-2-Aminocyclopentanecarboxylic acid is utilized as a key component in the development of biologically active compounds, potentially leading to the creation of new pharmaceuticals with therapeutic applications in various medical fields.

Upstream product

• 186249-66-1 (1S,2R)-2-phthalimidocyclopentane-1-carboxylic acid 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 1442488-69-8 benzyl (1R,2R)-2-formylcyclopentyl-N-hydroxycarbamate 
• 6140-65-4 1-cyclopentene-1-carboxaldehyde 
• 1442488-68-7 benzyl (3aS,6aR)-3-oxohexahydro-1H-cyclopenta[c]isoxazole-1-carboxylate 
• 1442488-67-6 benzyl (3R,3aS,6aR)-3-hydroxyhexahydro-1H-cyclopenta[c]isoxazole-1-carboxylate 
• 186249-62-7 2-[(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclopentyl]-isoindole-1,3-dione 
• 186249-65-0 2-((1R,2S)-2-Hydroxymethyl-cyclopentyl)-isoindole-1,3-dione 
• 186249-59-2 (1S,2R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclopentanol 
• 1883-85-8 trans-2-(hydroxymethyl)cyclopentanol 
• 163705-82-6 2--amino-1-carbobenzoxycyclopentene 
• 420123-96-2 (-)-4-aza-3-oxa-4-benzyl-2-spiro(1',3'-dithiane-[1'S,3'S]-1',3'-dioxo)-[5R,9S]-bicyclo[3.3.0] octane 
• 420123-95-1 (+)-2-(5,5-dimethoxy-pentylidene)-[1S,3S]-1,3-dioxo-dithiane 
• 50789-30-5 5,5-dimethoxypentanal 

Downstream Products

• 137170-89-9 (1S,2R)-2-((tert-butoxycarbonyl)amino)cyyclopentane-1-carboxylic acid 
• 958227-67-3 (1S,2R)-2-(5-bromo-2-{4-[methyl-(1-methyl-piperidin-4-yl)-carbamoyl]-phenylamino}-pyrimidin-4-ylamino)-cyclopentanecarboxylic Acid 

Relevant academic research and scientific papers

Stereoselective organocatalytic approach to α,β-disubstituted- β-amino acids: A short enantioselective synthesis of cispentacin

α-Branched α,β-unsaturated aldehydes have been tested in the organocatalytic tandem Michael addition/cyclization with N-(benzyloxycarbonyl)hydroxylamine, a reaction which until now has been restricted to α-unsubstituted enals. Starting from cyclopentene-2- carbaldehyde, and using diphenylprolinol trimethylsilyl ether as a chiral amine catalyst, this approach has led to the development of a practical, high yielding (93-98 % overall yield, three steps), and highly enantioselective (up to 98:2 er) route to the cyclic β-amino acid cispentacin, which compares favourably with previously described asymmetric syntheses of this biologically active natural product. When using acyclic α-branched α,β-unsaturated aldehydes as substrates, the reaction yields depend on the substitution pattern of the aldehydes, and mixtures of cis- and trans-isomers are obtained. Nevertheless, this strategy has proved to be successful in some instances, and (3R,4R)-benzyl 3-ethyl-4-methyl-5-oxoisoxazolidin-2-carboxylate could be obtained in 70 % overall yield (two steps) from the reaction of 2-ethylcrotonaldehyde and N-(benzyloxycarbonyl)hydroxylamine under catalysis with diphenylprolinol trimethylsilyl ether, and with high enantiomeric purity (99:1 er). The organocatalytic tandem Michael addition/cyclization of cyclopentene-2-carbaldehyde with N-Cbz-hydroxylamine, using diphenylprolinol TMS ether as a chiral amine catalyst, gives a practical, high yielding, and highly enantioselective route to the cyclic β-amino acid cispentacin. Acyclic α-branched enals give variable results in the same reaction, depending on the substitution pattern. Copyright

Highly Diastereoselective Nitrone Cycloaddition onto a Chiral Ketene Equivalent: Asymmetric Synthesis of Cispentacin

matrix presented A highly diastereoselective intramolecular nitrone cycloaddition onto a chiral ketene equivalent, obtained by Horner-Wadsworth-Emmons olefination of either enantiomer of bis-sulfinyl phosphonate 6, is described. Cycloaddition gave 5,5-disubstituted isoxazolidine 10 in good yield as a single diastereomer. Catalytic hydrogenolysis of 10 furnished either enantiomer of optically pure cis-2-aminocyclopentane-1-carboxylic acid.

An improved synthesis of enantiopure β-amino acids

An improved method for the preparation of both the enantiopure β-amino acids is presented. The diastereomer benzyl β-amino esters, obtained by stereoselective reduction of β-enamino esters, were separated and hydrogenolyzed to the free enantiopure β-amino acids.

Dolastatin 15 derivatives

Compounds of the present invention include cell growth inhibitors which are peptides of Formula I and acid salts thereof, wherein A, D, and E are α-amino acid residues, B is an α-amino acid residue or an α-hydroxy acid residue, F is an aminobenzoic acid r

Chemoenzymatic synthesis of both enantiomers of cispentacin

Based on the lipase-catalysed kinetic resolution of the silyloxyalcohol (1RS,2SR)-5 by transesterification with vinyl acetate in the presence of lipase from Pseudomonas cepacia a synthesis of both enantiomers of the β-amino acid cispentacin (1R,2S)-1 and (1S,2R)-1 using simple functional group interconversions is described.

Stereoselective reduction of enantiopure β-enamino esters by hydride: A convenient synthesis of both enantiopure β-amino esters

The reduction of enantiopure β-enamino esters 1 with sodium triacetoxyborohydride in acetic acid is described. This occurs with good diastereo- and enantioselectivity to yield β-amino esters 2 and 3 (after hydrogenolysis of the N-chiral group). A model is

Diastereo and Enantioselective Entry to β-Amino Esters by Hydride Reduction of Homochiral β-Enamino Esters.

The reduction of homochiral β-enamino esters 1 with sodium triacetoxyborohydride, which occurs with good diastereo- and enantioselectivity in the β-amino esters 2, is described.The procedure allows a straightforward preparation of compounds with known bio

Probing a Molecular Model of Taste Utilizing Peptidomimetic Stereoisomers of 2-Aminocyclopentanecarboxylic Acid Methyl Ester

On the basis of the preferred conformations of L-aspartyl dipeptide derivatives containing α-amino acids at the second position and their retro-inverso analogues deduced by a combination of X-ray crystallography, 1H NMR spectroscopy, and molecular mechani