83623-78-3

Usage

Uses

Used in Organic Chemistry:
(4S)-1-BOC-4-BENZYL-L-PROLINE is used as a building block in organic synthesis processes for its structural complexity and utility.
Used in Pharmaceutical Development:
(4S)-1-BOC-4-BENZYL-L-PROLINE is used as a key component in the development of drugs and pharmaceutical products, contributing to the creation of new and innovative treatments.
Used in Peptide and Protein Synthesis:
(4S)-1-BOC-4-BENZYL-L-PROLINE is used as a constituent in the synthesis of peptides and proteins, playing a crucial role in the formation of these biologically significant molecules.

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-/m0/s1

Upstream product

• 540501-26-6 (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine 
• 220993-22-6 (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate 
• 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 

Relevant academic research and scientific papers

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.