540501-62-0

Basic information

• Product Name: (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline
• CAS NO: 540501-62-0
• Molecular Weight: 257.33
• Mol File: 540501-62-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline(540501-62-0)
• EPA Substance Registry System: (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline(540501-62-0)

Safety Data

• Hazardous Substances Data: 540501-62-0(Hazardous Substances Data)

Upstream product

• 540501-24-4 (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-propylenepyrrolidine 
• 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 
• 96314-28-2 (2S,4R)-1-(tert-butoxycarbonyl)-4-(tosyloxy)pyrrolidine-2-carboxylic acid 
• 213475-89-9 (2S,4S)-2-allyl-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester 
• 213476-05-2 (2S,4S)-4-allyl-5-oxopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 365973-11-1 (2S,4S)-4-Allyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 59279-60-6 dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 663956-65-8 1-tert-butyl 2-methyl (2S,4S)-4-allyl-1,2-pyrrolidinedicarboxylate 
• 934470-75-4 1-tert-butyl 2-methyl (2S,4S)-4-propyl-1,2-pyrrolidinedicarboxylate 

Relevant articles and documents

Design and synthesis of long-acting inhibitors of dipeptidyl peptidase IV

A series of (4-substituted prolyl)prolinenitriles were synthesized and evaluated as inhibitors of dipeptidylpeptidase IV (DPP-IV). Among those tested, the 4β-[4-(hydroxyphenyl)prolyl]prolinenitriles showed a potent inhibitory activity with a long duration

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.