103290-39-7

Usage

Uses

Used in Drug Development:
(2R,4S)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid is used as a building block for the synthesis of pharmaceutical compounds, particularly in the development of new drugs. Its unique structure and stereochemistry enable the creation of complex molecules with specific biological activities.
Used in Biochemical Research:
(2R,4S)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid is used as a research tool in biochemical studies, allowing scientists to investigate the properties and functions of proline-containing peptides and proteins. Its use as a protecting group in peptide synthesis facilitates the study of peptide structure and function.
Used in Peptide and Protein Synthesis:
(2R,4S)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid is used as a protecting group in the synthesis of peptides and proteins, enabling selective chemical reactions and facilitating the production of complex molecular structures. Its temporary blocking of the amine group of proline allows for controlled and efficient synthesis processes.

Upstream product

• 96314-28-2 (2S,4R)-1-(tert-butoxycarbonyl)-4-(tosyloxy)pyrrolidine-2-carboxylic acid 
• 591-51-5 phenyllithium 
• 103290-38-6 C₁₇H₂₂NO₇S^(1-)*Li⁽¹⁺⁾ 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1356352-00-5 C₂₀H₂₉NO₄ 
• 96314-26-0 trans-4-phenyl-L-proline 
• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 35418-16-7 L-t-butyl pyroglutamate 

Downstream Products

• 1029259-64-0 tert-butyl (S)-1-((2S,4S)-2-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamoyl)-4-phenylpyrrolidin-1-yl)-1-oxonon-8-en-2-ylcarbamate 
• 1029259-55-9 C₃₂H₄₄N₄O₇S 
• 914662-37-6 (2S,4S)-N-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropyl)-4-phenylpyrrolidine-2-carboxamide hydrochloride 
• 175229-11-5 tert-butyl (2S,4S)-2-(hydroxymethyl)-4-phenylpyrrolidine-1-carboxylate 
• 954377-47-0 (2S,4S)-2-methanesulfonyloxymethyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 954377-48-1 (2R,4S)-2-methyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 954377-50-5 (2R,4S)-2-methyl-4-phenyl-1-propyl-pyrrolidine 
• 954377-49-2 (2R,4S)-2-methyl-4-phenyl-pyrrolidine 

Relevant academic research and scientific papers

LITHIUM DIPHENYLCUPRATE REACTIONS WITH 4-TOSYLOXY-L-PROLINES; AN INTERESTING STEREOCHEMICAL OUTCOME. A SYNTHESIS OF TRANS-4-PHENYL-L-PROLINE.

The reaction of lithium diphenylcuprate with trans-4- and cis-4-tosyloxy-L-prolines gives excellent yields of 4-phenyl substituted L-prolines and the reaction proceeds with net retention of configuration at the carbon center bearing the tosyloxy group.

PYRROLIDINE GPR40 MODULATORS

The present invention provides compounds of Formula (I): or a stereoisomer, a tautomer, a pharmaceutically acceptable salt, a polymorph, or a solvate thereof, wherein all of the variables are as defined herein. These compounds are GPR40 G protein-coupled receptor modulators which may be used as medicaments.

Discovery of a novel class of potent and orally bioavailable sphingosine 1-phosphate receptor 1 antagonists

A series of subtype selective sphingosine 1-phosphate receptor 1 (S1P 1) antagonists are disclosed. Our high-throughput screening campaign revealed hit 1 for which an increase in potency and mouse oral exposure was achieved with minor modifications to the chemical scaffold. In vivo efficacy revealed that at high doses compounds 12 and 15 inhibited tumor growth. Further optimization of our lead series led to the discovery of proline derivatives 37 (XL541) and 38 which had similar efficacy as our first generation analogues at significantly lower doses. Analogue 37 displayed excellent pharmacokinetics and oral exposure in multiple species.

SPHINGOSINE-1-PHOSPHATE RECEPTOR ANTAGONISTS

This disclosure relates to sphingosine-1 -phosphate (SlP) receptor antagonists, compositions comprising the SlP receptor antagonists and methods for using and processes for making the SlP receptor antagonists. In particularly, this disclosure relates to sphingosine-1 -phosphate 1 (SlPl) receptor antagonists, compositions comprising the SlPl receptor antagonist and methods for using the SlPl receptor antagonist, such as in the treatment of cancer, and processes for making the SlPl receptor antagonists.