462124-94-3

Usage

Type of compound

Derivative of pyrrolidine carboxylic acid

Chirality

(2S,3S)

Physical state

White to off-white solid

Molecular weight

305.37 g/mol

Usage

Chiral building block in organic synthesis

Applications

Preparation of various pharmaceuticals and biologically active compounds

Known for

Development of new drugs and pharmaceutical products

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 118758-49-9 (2S,3S)-3-phenyl-pyrrolidine-2-carboxylic acid 
• 1426559-89-8 C₁₁H₁₃NO₂*ClH 
• 143979-44-6 1-(tert-butoxycarbonyl)-3-phenylproline 
• 515173-98-5 (2S,3S)-3-phenyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 14371-10-9 (E)-3-phenylpropenal 
• 3005-63-8 1-acetyl-5-hydroxy-3-phenyl-pyrrolidine-2,2-dicarboxylic acid diethyl ester 
• 51212-36-3 1-acetyl-3-phenyl-pyrrolidine-2,2-dicarboxylic acid diethyl ester 
• 1187592-02-4 C₁₆H₂₁NO₃ 

Downstream Products

• 1449586-26-8 (2S,3S)-1-tert-butoxycarbonyl-3-cyclohexylpyrrolidine-2-carboxylic acid 
• 515173-98-5 (2S,3S)-3-phenyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 

Relevant academic research and scientific papers

Access to enantiomerically pure cis- and trans-β-phenylproline by high-performance liquid chromatography resolution

The preparation of all four stereoisomers of the proline analog that bears a phenyl group attached to the β carbon either cis or trans to the carboxylic acid (cis- and trans-β-phenylproline, respectively) has been addressed. The methodology developed allows access to multigram quantities of the target amino acids in enantiomerically pure form and suitably protected for use in peptide synthesis. Racemic precursors of cis-β-phenylproline and trans-β-phenylproline were prepared from easily available starting materials and subjected to high-performance liquid chromatography enantioseparation. Semipreparative columns (250 × 20 mm) containing chiral stationary phases based on amylose (Chiralpak IA) (Daicel-Chiral Technologies Europe, Illkirch, France) or cellulose (Chiralpak IC) were used respectively for the resolution of the cis- and trans-β-phenylproline precursors. Chirality, 24:1082-1091, 2012. 2012 Wiley Periodicals, Inc. Copyright

Diphenylprolinol silyl ether as a catalyst in an asymmetric, catalytic, and direct michael reaction of nitroethanol with α,β-unsaturated aldehydes

Diphenylprollnol silyl ether was found to be an effective organocatalyst in the enantioselective and direct Michael reaction of nitroethanol and α,β-unsaturated aldehydes, affording the 1-hydroxy-trans-3,4- disubstituted tetrahydropyrans after isomerizatl

Boronic ester and acid compounds, synthesis and uses

Disclosed herein are boronic ester and acid compounds, their synthesis and uses. More specifically, disclosed herein is a method for reducing the rate of degradation of proteins in an animal comprising contacting cells of the animal with certain boronic ester and acid compounds.

A convenient synthetic route to macrocyclic cis-3-phenylproline derivatives as mimics of Sandostatin

Enantiomerically pure 14- and 20-membered cyclic proline derivatives 2a- d were conveniently prepared from cis-3-phenylproline using macrolactonisation or macrolactamisation reactions.

BORONIC ESTER AND ACID COMPOUNDS

Disclosed herein is a method for reducing the rate of degradation of proteins in an animal comprising contacting cells of the animal with certain boronic ester and acid compounds. Also disclosed herein are novel boronic ester and acid compounds, their synthesis and uses.