158459-13-3

Usage

Uses

Used in Organic Synthesis:
(4R)-1-N-BOC-4-BENZYL-D-PROLINE is used as a chiral building block for the synthesis of various bioactive molecules. Its unique structure allows for the creation of complex organic compounds with specific stereochemistry, which is crucial for the development of new pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (4R)-1-N-BOC-4-BENZYL-D-PROLINE serves as a key intermediate in the synthesis of pharmaceutical compounds. Its ability to provide chiral centers and protect amine functionality makes it a valuable component in the development of enantiomerically pure drugs, which can have significant implications for the efficacy and safety of medications.
Used in Drug Development:
(4R)-1-N-BOC-4-BENZYL-D-PROLINE is utilized in drug development as a precursor for the synthesis of chiral drugs. Its presence in the synthesis process ensures that the final product has the desired stereochemistry, which is essential for the drug's biological activity and therapeutic effects. (4R)-1-N-BOC-4-BENZYL-D-PROLINE contributes to the advancement of innovative drug candidates with improved potency, selectivity, and reduced side effects.

InChI:InChI=1/C17H23NO4/c1-17(2,3)22-16(21)18-11-13(10-14(18)15(19)20)9-12-7-5-4-6-8-12/h4-8,13-14H,9-11H2,1-3H3,(H,19,20)/t13-,14-/m1/s1

Upstream product

• 1279049-67-0 cis-4-benzyl-L-proline hydrochloride 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 100-39-0 benzyl bromide 
• 400626-71-3 2-benzyl 1-(tert-butyl) (R)-5-oxopyrrolidine-1,2-dicarboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 125653-58-9 (2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 61478-26-0 tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 170947-82-7 ethyl (2S,4S)-N-BOC-4-benzylprolinate 
• 393524-67-9 γ-benzyl-L-proline 
• 1356352-02-7 C₂₁H₃₁NO₄ 
• 540501-37-9 (S)-2-Hydroxymethyl-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 171038-43-0 ethyl (2S,4R)-N-BOC-4-benzylprolinate 

Relevant academic research and scientific papers

MASP-2 INHIBITORS AND METHODS OF USE

The present disclosure provides, inter alia, compounds with MASP-2 inhibitory activity, compositions of such compounds and methods of making and using such compounds.

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.

NITROGEN-CONTAINING COMPOUNDS

A compound represented by formula (I); wherein ring A represents a nitrogen containing heterocyclic ring, ring B represents 5-membered heterocyclic ring which may have substituents, R represents a hydrogen atom or cyano and the other symbols represent as

Design, synthesis, and evaluation of proline based melanocortin receptor ligands

A series of proline based melanocortin ligands has been developed on the basis of initial piperazine leads by using a more conformationally rigid scaffold. A number of these novel ligands showed significant binding affinity for MC3 and MC4 receptors.

Asymmetric hydrogenations for the synthesis of boc-protected 4-alkylprolinols and prolines

The utility of 4-substituted prolinols and their corresponding prolines in peptides, peptidomimetics, and natural products has motivated researchers to find new and efficient routes for their preparation. Herein, we report a general approach to the synthesis of Boc-protected 4-alkylprolinols and prolines via a divergent asymmetric hydrogenation strategy. Intermediate exocyclic olefins were prepared by Wittig-type reactions with ketone 6 and subjected to hydroxyl and sterically directed reductions. The Crabtree catalyst (Ir[COD] PyPCy3PF6) proved to be highly effective in diastereoselective hydrogenations to give trans- substituted pyrrolidines (9). Good facial selectivities were also observed in heterogeneous hydrogenations with Raney-nickel to obtain cis-substituted pyrrolidines (11). Employing this strategy, we describe the synthesis of novel prolinol and proline-based building blocks for incorporation into biologically relevant peptidomimetics.

PHOSPHINYLALKANOYL SUBSTITUTED PROLINES

Esters of phosphinylalkanoyl prolines and phosphinylalkanoyl substituted prolines are inhibitors of angiotensin converting enzyme and are useful in the treatment of hypertension.