959583-52-9

Basic information

• Product Name: (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid
• Synonyms: (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid;(Tert-Butoxy)Carbonyl (R)-γ-(4-fluoro-benzyl)-L-Pro
• CAS NO: 959583-52-9
• Molecular Formula: C₁₇H₂₂FNO₄
• Molecular Weight: 323.3592832
• Product Categories: unnatural amino acids
• Mol File: 959583-52-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 123-125℃
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid(959583-52-9)
• EPA Substance Registry System: (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid(959583-52-9)

Safety Data

• Hazardous Substances Data: 959583-52-9(Hazardous Substances Data)

Usage

General Description

"(2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid" is a complex organic compound, typically used in various fields of chemical research and development. Its structure consists of a pyrrolidine ring, a type of cyclic amine, combined with different functional groups such as a tert-butoxycarbonyl (a type of carbamate protecting group), a 4-fluorobenzyl group, and a carboxylic acid at the 2nd position of the ring. The compound’s stereospecificity, denoted by (2S,4R), indicates its specific spatial configuration. It is a critical component in the synthesis of peptides and other complex organic molecules. Outside property data like its density, boiling point, or melting point could vary based on its purity and specific isomers.

Upstream product

• 35418-16-7 L-t-butyl pyroglutamate 
• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 1356352-04-9 C₂₁H₂₈FNO₅ 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1049977-93-6 (2S,4R)-4-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid 

Downstream Products

• 1221878-02-9 (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide 
• 1221878-06-3 XL₅₄₁ 
• 1221877-81-1 (2S,4R)-1-(2-(2H-1,2,3-triazol-2-yl)acetyl)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide 
• 1222196-66-8 (2S,4R)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide 
• 1356352-22-1 (2S,4R)-tert-butyl 4-(4-fluorobenzyl)-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate 

Relevant articles and documents

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.